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  • 1980-1984  (3,496)
  • 1965-1969  (3,164)
  • 1955-1959  (2,453)
  • 1950-1954  (2,076)
  • Organic Chemistry  (11,064)
  • Insulin
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  • 1
    Electronic Resource
    Electronic Resource
    Studies on acute glucose-induced aldosterone suppression: Role of renin-angiotensin system (1984)
    Springer
    Journal of molecular medicine 62 (1984), S. 213-217 
    Details
    ISSN: 1432-1440
    Keywords: Aldosterone ; Glucose ; Insulin ; Potassium ; Renin-angiotensin system ; Cortisol ; Captopril
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Glucose loading is known to cause acute suppression of plasma aldosterone and stimulation of plasma renin activity. The relative contribution of variations in circulating angiotensin II to the regulation of aldosterone secretion following glucose loading was assessed in ten normal subjects. The effects of a standard oral glucose loading test (100 g) on plasma concentrations of glucose, insulin, potassium, aldosterone, renin activity and cortisol were studied (a) under basal conditions, and (b) after inhibition of angiotensin II with the converting enzyme inhibitor captopril (50 mg t.i.d. during 3 days). Under basal conditions the acute increase in plasma glucose and insulin after glucose loading was accompanied by a significant decrease (P〈0.01) in plasma cortisol and aldosterone and by a significant increase in plasma renin activity (P〈0.01); plasma potassium was decreased slightly but not significantly. Following captopril treatment preloading plasma renin activity was increased significantly, most probably reflecting an effective reduction of angiotensin II. Glucose loading caused a similar suppression of plasma aldosterone, as observed under basal conditions. This observation suggests that renin activation does not substantially contribute to the acute regulation of plasma aldosterone after an oral glucose load.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01721046
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  • 2
    Electronic Resource
    Electronic Resource
    Neurotensin — Was ist gesichert über seine Rolle als Hormon im Magen-Darmtrakt? (1984)
    Springer
    Journal of molecular medicine 62 (1984), S. 523-530 
    Details
    ISSN: 1432-1440
    Keywords: Neurotensin ; Gastrointestinal hormones ; Gastric secretion ; Pancreatic secretion ; Motility ; Insulin ; Glucagon
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Neurotensin is a tridecapeptide originally isolated and characterized from bovine hypothalamus and later, in identical form, from bovine and human intestine. In the rat about 85% of immunoreactive neurotensin is found in the gut and about 10% in the brain. When an antibody specific for the amino terminal region of neurotensin was used the highest concentrations were found in the mucosa of the ileum, while an antibody specific for the biologically active region, the carboxyl terminus, also detected large amounts in the mucosa of the upper gastrointestinal tract. After a meal neurotensin — as measured by carboxyl terminal antibodies — rises after 5 min, a time in which the chymus has not yet reached the ileum, the main source of whole neurotensin. It is therefore possible that the carboxyl terminal molecules of neurotensin, found in the upper gastrointestinal tract, play an important physiological role. In plasma, neurotensin is rapidly degraded into smaller amino terminal and therefore biologically inactive molecules. Increases of carboxyl terminal neurotensin have been found in plasma in only a very few studies. The nature of this immunoreactive material has not yet been established. Therefore, the physiological role of neurotensin as a circulating hormone is unknown. Potential actions of neurotensin include thermoregulation, regulation of hormone release from brain (pituitary hormones) and gut (glucagon, insulin, somatostatin, pancreatic polypeptide), increase of vascular permeability, vasodilatation, inhibition of gastric acid secretion, stimulation of pancreatic secretion and changes of gut motility from the fasting to the fed type.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01727746
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  • 3
    Electronic Resource
    Electronic Resource
    Effect of continuous and oscillatory portal vein insulin infusion upon glucose-induced insulin release in rats (1984)
    Springer
    Research in experimental medicine 184 (1984), S. 67-71 
    Details
    ISSN: 1433-8580
    Keywords: Oscillations ; Insulin ; Glucose
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The present study was designed to determine the effect of low dose continuous and oscillatory intraportal insulin infusions upon subsequent glucose-induced insulin release. In overnight-fasted and anesthetized rats with indwelling catheters in the jugular vein, carotic artery, and mesenteric vein insulin was infused intraportally for 3 h via the mesenteric vein catheter at a continuous rate of 45 µU/kg·min, or the same amount of insulin was administered at alternating high (72 µU/kg·min) and low infusion rates (18 µU/kg·min), respectively, in 2-, 4-, 8-, and 16-min cycles (oscillatory infusions). Another group received a continuous infusion of saline. Glucose (0.4 g/kg) was given i.v. 30 min after the end of the insulin or saline infusion. During the 3-h infusion of insulin or saline the peripheral glucose level remained unchanged in all groups. In response to the i.v. glucose load peripheral arterial plasma insulin levels were significantly elevated after preceding oscillatory infusions compared to the continuous insulin infusion. As compared to the group receiving saline the glucose-induced insulin response after continuous insulin infusion was significantly reduced. The plasma glucose responses were not different except for inexplicably elevated glucose levels in the 4-min cycle group. No difference was observed for plasma glucagon levels in all groups. The present data demonstrate an augmented responsiveness of theβ-cell to glucose after a preceding oscillatory infusion of insulin and an impaired responsiveness to glucose after continuous insulin infusion. This indicates that an oscillatory insulin release might be of importance for an adequate regulation ofβ-cell function.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01852224
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  • 4
    Electronic Resource
    Electronic Resource
    Effect of contact material on vibration-induced insulin aggregation (1984)
    Springer
    Diabetologia 27 (1984), S. 373-378 
    Details
    ISSN: 1432-0428
    Keywords: Insulin ; administration and dosage ; therapeutic use ; insulin infusion devices
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The tendency of insulin to form insoluble aggregates is a major obstacle to the development of implantable insulin infusion systems for treatment of insulin-deficient diabetic patients. A test system was developed to examine the kinetics of insulin aggregation under controlled conditions of temperature, vibration and contact material in an effort to provide design criteria for minimising aggregation. The contact materials tested were all potentially suitable for pump reservoirs on engineering criteria and included metals (stainless steel, titanium and a titanium alloy) and various plastics (polypropylene, polytetrafluoroethylene, Polyvinylchloride, polyamide, cellulose butyrate and silicone elastomer). The rate of insulin aggregation was markedly affected by the nature of the contact material. Hydrophilic materials, particularly polyamide and cellulose butyrate (2% of total insulin aggregated after 96 h vibration), appeared more compatible with insulin stability than did hydrophobic ones, such as polypropylene (16% aggregation) and Polyvinylchloride (37% aggregation). A specially formulated ‘pump’ insulin preparation, stabilised by addition of polyethylenepolypropyleneglycol, was significantly superior (three to five times more stable) to a regular neutral insulin formulation under most, but not all, conditions. Standard clinical syringes (polypropylene) performed poorly with both insulin formulations but especially with the neutral regular insulin (100% aggregation after 96 h vibration). In addition to physical aggregates, significant amounts (5%–30%) of the insulin remaining in solution were no longer detectable by immuno- or receptorassay in all materials tested. Appropriate combinations of insulin formulations and materials can minimise insulin aggregation and denaturation, but since the mechanisms involved are as yet poorly understood, realistic testing of proposed reservoir components and insulin formulations must be a prerequisite in insulin infusion pump planning and design. These testing procedures should be designed to test for denaturation in solution as well as for precipitation of insulin.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00304853
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  • 5
    Electronic Resource
    Electronic Resource
    Factors governing the human immune response to injected insulin (1984)
    Springer
    Diabetologia 26 (1984), S. 266-271 
    Details
    ISSN: 1432-0428
    Keywords: Insulin ; insulin antibody ; immunogenicity ; immune response genes ; haemocyanin ; HLA ; DR7 ; C2 ; C4 ; factor B ; Gm ; C-peptide
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Seventy-nine patients were observed prospectively during their initial period of treatment with conventional bovine insulins. Insulin antibody levels 6 months after starting insulin therapy did not correlate with age, gender or β cell function at onset of treatment. Patients who required soluble insulin in addition to isophane insulin developed higher levels of insulin antibody. Patients bearing the HLA-B8, DR3 and C4AQO alleles had lower levels of insulin antibody, whereas those bearing DR7 produced significantly higher levels. Other alleles at the C4A, C4B, C2, factor B or Gm loci did not appear to have a significant effect on insulin antibody production. The hyporesponsiveness of B8/DR3/C4AQO-positive individuals probably reflects a non-specific abnormality of immunity whereas the enhanced responsiveness of those positive for DR7 suggests the presence of a specific immune response gene for insulin
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00283648
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  • 6
    Electronic Resource
    Electronic Resource
    Effect of co-ingestion of fat on the metabolic responses to slowly and rapidly absorbed carbohydrates (1984)
    Springer
    Diabetologia 26 (1984), S. 50-54 
    Details
    ISSN: 1432-0428
    Keywords: Insulin ; gastric inhibitory polypeptide ; insulin sensitivity ; glucose tolerance ; diabetes ; diet ; fat ; rate of carbohydrate digestion
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The present study examined the acute effects of coingestion of fat (37.5 g) on the post-prandial metabolic responses to 75 g of carbohydrate which was either slowly absorbed (lentils) or rapidly absorbed (potatoes). Co-ingestion of fat resulted in a significant flattening of the post-prandial glucose curves, the effect being more pronounced for the rapidly absorbed potatoes. This was probably due to delayed gastric emptying. However, the post-prandial insulin responses to either carbohydrate were not significantly reduced by fat, suggesting that the insulin response to a given glucose concentration was potentiated in the presence of fat. The gastric inhibitory polypeptide (GIP) responses to both carbohydrates were greatly increased in the presence of fat. To investigate further the possible roles of GIP in the entero-insular axis, a 5-g bolus of glucose was injected intravenously 1 h after lentils ± fat. This was sufficient to raise the glucose levels above the threshold reported for GIP to potentiate insulin secretion. However, despite the large differences in circulating GIP levels, the insulin response to glucose was not affected by the presence of fat. These results suggest that (1) the rate of absorption of carbohydrate is a major determinant of post-prandial metabolic responses even in the presence of fat, (2) fat-stimulated GIP secretion does not potentiate glucose-induced insulin secretion, and (3) the potentiation of the insulin response to glucose when carbohydrate is co-ingested with fat is consistent with the well-documented insulin resistance associated with high fat diets.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00252263
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  • 7
    Electronic Resource
    Electronic Resource
    Evidence for post-transcriptional regulation by insulin of 3-hydroxy-3-methylglutaryl coenzyme A reductase and sterol synthesis in human mononuclear leucocytes (1984)
    Springer
    Diabetologia 26 (1984), S. 366-369 
    Details
    ISSN: 1432-0428
    Keywords: Insulin ; 3-hydroxy-3-methylglutaryl coenzyme A ; sterol synthesis ; human mononuclear leucocytes ; post-transcriptional regulation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Incubation of freshly isolated human mononuclear leucocytes in lipid-depleted serum for 4 h resulted in a two-fold increase in 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase activity. Insulin, when added to the incubation medium at concentrations of 10 and 100 nmol/l at zero time, caused additional increases in the enzyme activity of 30% and 37%, respectively. The hormone action was not immediate because no effect was observed when insulin was added at 4 h and activity examined thereafter. Under these conditions sterol synthesis from 14C-acetate and tritiated water was strictly proportional to the activity of HMG-CoA reductase. Cycloheximide (20 μg/ml), a translational inhibitor of protein synthesis, prevented the insulin-mediated increase in the enzyme activity and the incorporation of 14C-acetate into sterols. Cordycepin (50 μg/ml) inhibited messenger RNA synthesis by 〉 50%, but had no inhibitory effect on the induction of HMG-CoA reductase and sterol synthesis. Low density lipoprotein (80 μg protein/ml) and complete serum blocked the induction of the enzyme and sterol synthesis from 14C-acetate caused by lipid-depleted serum. The insulin-effect, however, remained unchanged. The results suggest that insulin may regulate the de novo synthesis of HMG-CoA reductase and accordingly sterol synthesis at a post-transcriptional level.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00266038
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  • 8
    Electronic Resource
    Electronic Resource
    Inotropic effect of prenalterol in amitriptyline poisoning (1984)
    Springer
    Intensive care medicine 10 (1984), S. 209-211 
    Details
    ISSN: 1432-1238
    Keywords: Amitriptyline ; Hydrocortisone ; Insulin ; Prenalterol ; Cardiac failure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract A case of severe amitriptyline poisoning with grade IV coma, seizures, bradycardia and hypotension who did not respond to dopamine was successfully treated with prenalterol, a new cardioselective β-agonist. The case is discussed with respect to plasma concentrations of dopamine, prenalterol and amitriptyline. Prenalterol, hydrocortisone and insulin may be useful as inotropic agents in tricyclic poisoning where dopamine fails to provide an adequate response.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00259441
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  • 9
    Electronic Resource
    Electronic Resource
    Vanadate stimulates the pumped movements of Na in skeletal muscle (1984)
    Springer
    Pflügers Archiv 400 (1984), S. 413-417 
    Details
    ISSN: 1432-2013
    Keywords: Sodium pump ; Na-K ATPase ; Na fluxes ; Vanadate ; Insulin ; Skeletal muscle ; Ouabain
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract We have measured the effects of concentrations of vanadate ranging between 0.01 and 10 mM on the22Na efflux of frog sartorius muscles. The addition of vanadate had no effects when concentrations lower than 0.5 mM were used; higher concentrations increased Na efflux. The increase was abolished by the addition of ouabain (10−5M). In muscles pretreated with ouabain vanadate did not modify Na efflux. The stimulatory effects of vanadate on Na efflux were also observed in Na-free solutions indicating that the effux of vanadate was not caused mainly either by an increase in the exchange of Na for Na or by an increase in Na entry into the muscle. We also examined the effects of vanadate on muscles immersed in solutions containing 20 mM K+; both vanadate and increased K+ produced stimulations of Na efflux that were additive. Similarly when the effects of vanadate and insulin were measured on the Na efflux of the same muscle, additive effects were found. As the ouabain-sensitive Na efflux in frog muscle is generally agreed to be due to the activity of the Na-K ATPase, our findings suggest that the net effect of vanadate in intact muscle cells is an increase in the activity of the Na pump. Since vanadate affects many enzymes it is quite possible that the stimulatory action is not due to a direct effect on the Na-K ATPase but may be mediated through an intermediary step. Regardless of the specific mechanism, it is evident that, our results as well as other findings in the literature, strongly indicate that Na pumping by intact cells can be increased by vanadate administration. Hence it is not justified to attribute the physiological modifications caused by vanadate administration to blockade of the Na-K ATPase unless the attribution is justified by specific experimental evidence.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00587542
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  • 10
    Electronic Resource
    Electronic Resource
    Energetics of active sodium-potassium transport following stimulation with insulin, adrenaline or salbutamol in rat soleus muscle (1984)
    Springer
    Pflügers Archiv 401 (1984), S. 160-166 
    Details
    ISSN: 1432-2013
    Keywords: Biological transport ; Insulin ; Energy metabolism ; Epinephrine ; Endocrinology ; Albuterol (salbutamol) ; Active sodium-potassium transport ; Muscle
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The total metabolic energy expenditure associated with active Na−K-transport over the first 20 min of stimulation with insulin, adrenaline or salbutamol (ΔHmNa−K) was determined from direct calorimetric and tracer ion flux measurements in isolated muscles at rest. The reversible work performed by the Na−K-pump during the same interval of time (WrevNa−K) was calculated as the product of the ouabain-suppressible Na−K transfers and the mean free energy increase imparted to the two ions as they are transported against their electrochemical gradients across the plasma membrane. Comparison of membrane potential and intracellular Na and K concentrations before and after the stimulations indicated that part of WrevNa−K had contributed to increase the ion electrochemical gradients in the preparation (i.e. had not been lost as heat) during the 20 min period. Accordingly, the maximum value of ΔHmNa−K was taken as the sum of the ouabain-suppressible heat production and WrevNa−K. Following stimulation with insulin, adrenaline or salbutamol this maximum corresponded to 10, 10 and 12% respectively, of basal metabolism. Under the same three conditions, the minimum “energetic efficiency” of the active Na−K-transport process, defined as the ratio between WrevNa−K and maximum ΔHmNa−K, was 35, 41 and 38%, respectively.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00583876
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  • 11
    Electronic Resource
    Electronic Resource
    Long-term follow-up of children with craniopharyngioma (1984)
    Springer
    European journal of pediatrics 142 (1984), S. 179-185 
    Details
    ISSN: 1432-1076
    Keywords: Craniopharyngioma ; Growth ; Insulin ; Neurosurgery ; Radiotherapy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Management of craniopharyngiomas is still controversial. 28 children with this tumor were studied. GH deficiency was present in 22 patients following surgery, 10 of these GH-lacking patients had normal or accelerated growth (usually associated with rapid weight gain) postoperatively. Somatomedin levels were normal in three of six normally growing patients. After craniotomy their basal and TRH-stimulated prolactin levels were in the normal range, but their insulin secretion was markedly increased. Postoperatively there was a significant correlation between peak insulin levels following arginine infusion and growth velocity in all patients. Complete tumor removal could be performed in 28% of our patients. Altogether 36% of all patients had at least one tumor recurrence. Recent literature with the addition of our series showed tumor recurrence in 22% of patients with “total” tumor excision and in 72% of patients with partial tumor removal. Radiotherapy seems to be capable of destroying craniopharyngioma tissue. The recurrence rate was only 26% in patients with subtotal excision plus radiotherapy. Unless radical tumor removal can be attempted with safety, subtotal tumor removal plus radiotherapy appears to be the treatment of choice for craniopharyngioma.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00442445
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  • 12
    Electronic Resource
    Electronic Resource
    Effects of prolonged maternal fast on the pancreas of 18–21-day-old foetal rats (1984)
    Springer
    Cell & tissue research 237 (1984), S. 169-179 
    Details
    ISSN: 1432-0878
    Keywords: Foetal pancreas ; β Cells ; Insulin ; Fasting mothers ; Morphometry ; Rat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary After maternal fasting for 72 h the pancreatic β cells of 18-day-old foetal rats show a conspicuous enrichment in secretory material, with an increase of pancreatic insulin concentration and a marked development of the rough endoplasmic reticulum and the Golgi apparatus. The morphometric analysis shows that the intracytoplasmic migration of the secretory granules is inhibited, principally inside the cell web. Consequently the number of secretory granules fused with plasma membrane decreases and this is associated with a decreased foetal plasma insulin. The difference in the ultrastructural aspect of the β cells of foetuses from fasting mothers and of foetuses from fed mothers is less conspicuous at 19 days of gestation and progressively disappears at 20 and 21 days. The modifications in ultrastructural aspect and in functional state are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00229213
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  • 13
    Electronic Resource
    Electronic Resource
    Effects of a rapid change in muscle glycogen availability on metabolic and hormonal responses during exercise (1984)
    Springer
    European journal of applied physiology 53 (1984), S. 57-62 
    Details
    ISSN: 1439-6327
    Keywords: Muscle glycogen ; Time sequence ; Free fatty acids ; Insulin ; Exercise in humans
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary To evaluate the metabolic and hormonal adaptations following a rapid change in muscle glycogen availability, 14 subjects had their muscle glycogen content increased in one leg (IG) and decreased in the other (DG). In group A (n=7), subjects exercised on a bicycle ergometer at 70% maximal oxygen uptake for 20 min using the DG leg. Without resting these same subjects exercised another 20 min using the IG leg. Subjects in group B (n=7) followed the same single-leg exercise protocol but in the reverse order. In order to get some information on the time sequence of these possible adaptations, blood samples were collected at rest and at the beginning and the end of each exercise period (min 5, 20, 25, and 40). Results indicated that 5 min after the switch from the DG leg to the IG leg. transient increases in plasma free fatty acids (1.20 to 1.39 meq·l−1) and serum insulin (10.1 to 12 mU·l−1) concentrations occured. Between minute 25 and 40 of exercise, the DG to IG switch was accompanied by a decrease in free fatty acids and glycerol concentrations as well as an increase in lactate levels. An opposite response was observed in the IG to DG condition during the same time span. Plasma norepinephrine, epinephrine, glucagon, and serum cortisol concentrations were not significantly affected by the leg change. These results suggest a rapid preferential use of muscle glycogen when available and a time lag in the response of the extramuscular substrate mobilization factors.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00964691
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  • 14
    Electronic Resource
    Electronic Resource
    Metabolic and hormonal responses to prolonged physical exercise in dogs after a single fat-enriched meal (1984)
    Springer
    European journal of applied physiology 53 (1984), S. 267-273 
    Details
    ISSN: 1439-6327
    Keywords: Exercise ; Triglycerides ; Free fatty acids ; Glycerol ; Insulin ; Catecholamines
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Metabolic and hormonal responses to prolonged treadmill exercise in dogs fed a fat-enriched meal 4 h prior to the exercise were compared to those measured 4 h after a mixed meal or in the postabsorptive state. Ingestion of the fat-enriched meal caused significant elevations in the resting values of plasma triglyceride (TG), free fatty acid (FFA), and glycerol concentrations. A reduction of the plasma TG concentration (from 1.6±0.2 to 1.1±0.10 mmol·l−1,P〈0.005) occurred only in dogs exercising after the fat-enriched meal. No significant changes in this variable were noted in dogs fed a mixed meal, whilst in the postabsorptive state exercise caused an increase in the plasma TG level (from 0.42±0.03 to 0.99±0.11 mmol·l−1,P〈0.01). The exercise-induced elevations in plasma FFA and glycerol concentrations were the highest in the dogs given the fat-enriched meal. Plasma glycerol during exercise correlated with the initial values of circulating TG (r=0.73). The plasma FFA-glycerol ratio, at the end of exercise was lowest in the dogs taking the fat-enriched meal (1.39±0.19), suggesting an increased utilization of FFA in comparison with that in the postabsorptive state (3.27±0.37) or after a mixed meal (2.88±0.55). Basal serum insulin (IRI) concentrations were similarly enhanced in dogs fed fat-enriched and mixed meals, and they were reduced to control values within 60 min of exercise. Plasma adrenaline and noradrenaline concentrations correlated with time of exercise (r=0.84 andr=0.96, respectively) and were unaffected by the nutritional modifications. It is concluded that ingestion of a single fat-enriched meal considerably modifies the exercise-induced changes in lipid metabolism. The pattern of changes in plasma TG, FFA, and glycerol concentrations indicates an enhanced hydrolysis of plasma chylomicron-TG, suggesting that this lipid source may contribute markedly to exercise metabolism.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00776601
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  • 15
    Electronic Resource
    Electronic Resource
    Further increase in high density lipoprotein in trained males after enhanced training (1984)
    Springer
    European journal of applied physiology 52 (1984), S. 426-430 
    Details
    ISSN: 1439-6327
    Keywords: Apoproteins ; Lipoproteins ; Insulin ; Blood lactate ; Physical training
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Eight well-trained males were studied before, during and after 6 months of a progressively increased amount of endurance training in order to elucidate the effects on the apoproteins and apo-lipoproteins. Initially high HDL-cholesterol levels were revealed (1.62±0.15 mmol×l−1, mean ± SE.). After a transient but not significant, slight decline at the onset of the increased training program (1.57±0.06 mmol×l−1) HDL-cholesterol increased gradually to the end of the training period (1.92±0.12 mmol×l−1). There was an increased aerobic capacity as judged by maximal oxygen uptake and by lactate concentration during standardized submaximal work. However, at the end of the training period, a levelling off in maximal oxygen uptake was revealed, while HDL-cholesterol was still increasing. The present data demonstrate that HDL can be influenced by training at all levels of aerobic capacity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00943374
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  • 16
    Electronic Resource
    Electronic Resource
    The He(Iα) Photoelectron Spectra of the Perfluoroderivatives of Trisannelated Benzenes and Tetrakisannelated Cyclooctatetraenes (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 47-53 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The He(Iα) photoelectron (PE) spectra of tris(perfluorocyclobuta)benzene 4(F)3,3,4,4,7,7,8,8,11,11,12,12-Dodecafluorotetracyclo[8.2.0.02,5.06,9]dodeca-1,5,9-triene, tris(perfluorocyclopenta)benzene 5(F)1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-Octadecafluoro-2,3,4,5,6,7,8,9-octahydro-1H-trindene., tetrakis(perfluorocyclobuta)cyclooctatetraene 6(F)3,3,4,4,7,7,8,8,11,1l,l2,l2,l5,15,16,16-Hexadecafluoropentacyclo[12.2.0.02,5.06,9.010,13]hexadeca-1,5,9,13-tetraene., and of tetrakis(perfluorocyclopenta)cyclooctatetraene 7(F)1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12-Tetracosafluoro-1,2,3,4,5,6,7,8,9,10,11,12-dodeca-hydrotetracyclopenta[a,c,e,g]cyclooctene. are reported. A tentative assignment of the PE spectra is derived by empirical correlation with those of relevant reference compounds. The results suggest that 6(F) retains the D4h-conformation in the gas phase, i.e. A conformation with a planar cyclooctatetraene ring, as observed in the crystal. All four compounds exhibit a sharp increase of their first ionization energies, relative to the corresponding parent hydrocarbons, due to the perfluoro effect.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670107
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  • 17
    Electronic Resource
    Electronic Resource
    Transition metal complexes with bidentate ligands spanning trans-positions. Part XIVPart XIII: see [1].. Some complexes of 2,11-bis(diphenylphosphinomethyl)benzo[c]phenanthrene with platinum (0) and their reactivities (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 65-72 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The ligand 2,11-bis(diphenylphosphinomethyl)benzo[c]phenanthrene (1) has been used to prepare complexes of the type [PtL(1)] (L = C2H4, CH2=CH—CO2Me, PhC≡CPh, MeC≡CMe, MeO2CC≡CCO2Me, (i-Pr)O2CC≡CCO2(i-Pr), Ph3P and CO). It is shown that these complexes are less labile than the corresponding species [PtL(Ph3P)2]. The preparation of complexes trans-[PtX(R)(1)] by oxidative addition of RX (RX = PhCH2Br and Mel) to [Pt(C2H4)(1)] is described. The isolation of [PtO2(CH3)2CO(1)] is also reported.
    Additional Material: 3 Tab.
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    Intermolecular Electron Spin Transfer between Naphthalene π-Systems Separated by a Variable Number of Spirobonded Cyclobutane Rings, An. ESR and ENDOR Study (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 416-424 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The radical anions of the compounds N1N, N3N and N5N, in which two naphthalen π-systems are separated by 1, 3 and 5 spirobonded cyclobutane rings, respectively, and tha tof the reference compound N1, containing one naphthalene π-system and one cyclobutane ring, have been studied by ESR and ENDOR spectroscopy under a variety of experimental conditions. The intramolecular electrons spin transfer between the two π-moieties in N3N.⊖ and N5N.⊖ is slow on the hyperfine time-scale, irrespective of the applied conditions. It is also slow in N1N.⊖, except for media of high solvating power. In such media, with a slight reduction of N1N to its radical anion, a paramagnetic species is observed, the hyperfine data for which are consistent with N1N to its radical anion, a paramagnetic species is observed, the hyperfine data of which are consistent with N1N.⊖, undergoing a fast intramolecular electron spin tansfer. The ESR and ENDOR spectra of this species are superimposed on those characteristic of a slow transfer. It is suggested that the fast and slow transfer involve the syn- and anti-conformations, respectively, since the distance, r, between the two naphthalene π-systems of N1N.⊖ is considerably shorter in the former than in the latter (r = 740 vs. 880 Pm for the distance between the centres of the π-systems). Glassy solutions of exhaustively reduced N1N display signals of the dianion triplet state, whereas no such signals are found for N3N and N5N. The zero-field splitting parameter, D, is 4.7 mT, corresponding to r ≈ 480 pm.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670210
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  • 19
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    The mass spectra of organic compounds. 7th Communication6th Communication, see [1].. 4,4-Dimethyl-1-pentene (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 425-433 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Loss of CH3., CH4, C2H4, C3H5., C3H6 and C3H7 from the molecular ions of a number of 13C-labeled analogs of 4,4-dimethyl-1-pentene was studied both in normal (source) 70-eV electron impact (EI) spectra dn in metastable spectra. For loss of CH3. in the source, 96% of the methyl comes frm positions of 5, 5′ and 5″, while the remainder comes from position 1. In the metastable spectra, loss of C-1 (16%) and C-3 (9%) is increasing in importance. The loss of ethylene is a particular case: either C-1 or C-3 are lost with any other C-atom from positions 2,5,5′, and 5″ (8 × 10%) in the metastable spectra, the probability for simultaneous loss of C-1 and C-3 being 6%. If C-1 seems to these two positions become completely equivalent in the metastable time range. The T-values (kinetic energy release) for the different positions show small, but statisticaly different values and a small isotope effect. Loss of C3H5 (allylic cleavage) is 100% C-1, C-2 and C-3, i.e., no evidence for skeletal rearrangement is seen. This is also true for loss of C3C6 (McLafferty rearrangement) within the source, but in metastable decay the other positions gain in importance. The neutral fragment C3H7. appears to be the the result of consecutive loss of CH3. and C3H4, rather than a one-step loss of propyl radical or the inverse reactions sequence. No metastable reaction can be seen for this reaction. Decomposition of labeled C6H11+ and C5H10+ secondary ions occurs in an essentially random fashion.
    Additional Material: 6 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19840670211
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  • 20
    Electronic Resource
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    Synthese von para-substituierten phenyl-terpyridin liganden (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 450-454 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Up to now the synthesis of para-substituted phenyl-terpyridine ligands was difficult with respect to the purification of the reaction products. We have found that these compounds can easily be isolated as hydrobromides from acetic acid. Starting from the hydrobromides the purification turned out to be easy. Synthesis of para-substituted Cl-, Br-, H3C-, H2BrC-, HO- 2,6-Bis(2-pyridyl)-4-phenylphyridine is reported.
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    URL: http://dx.doi.org/10.1002/hlca.19840670214
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  • 21
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    Complexation de l'argent(I) par des teramines cycliques (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 441-449 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Complexation of Silver(I) by Cyclic TetraminesThe nature of Ag(I)-complexes with 1,4,8,11-tetraazacyclotetradecane (1), 1,5,9,13-tetraazacyclohexadecane (2) 1,5,10,14-tetraazacyclooctadencane (3) and 1,6,11,16-tetraazacycloeicosane (4) is studied. The effect of ring size on disproportionation of the Ag() cation in the presence of ligand is reported. The stability of Ag(I)-complexes with 3 and 4 in aqueous solution is determined by means of potentiometric titration.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670213
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  • 22
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    Mitteilungen - Communications (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 625-627 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670231
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    Masthead (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984) 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670301
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  • 24
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    Radikalionen von überbrückten [14] Annulenen. Untersuchungen zum Frontorbitaleinfluss auf Reaktivität und Bindungszustand (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 625-639 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Radical Ions of Bridged [14] Annulenes. Investigations on the Influence of Frontier Orbitals on Reactivity and BondingThe radical anions and the radical cations derived from trans-15, 16-dimethyl-1, 4:8,11-ethandiyliden[14]annulene (6), trans-15-methyl-1,4:8,11-ethandiyliden[14]annulene (7) and cis-15, 16-propano-1,4:8,11-ethandiyliden[14]annulene (8) are described. The hyperfine data of the radical anions 6, 7 and 8 resemble those of the structurally related radical anions of trans-10b, 10c-dimethyldihydropyrene (4) and trans-10b, 10c-dihydropyrene (5). This finding leads to the conclusion, that the change in the relative arragement of the saturated bridge within the fourteen-membered π-perimeter by passing from 4 (5) to 6 (7, 8) does not in fluence the energetic sequence of the lowest unoccupied molecular orbitals. The behavior of 6 and 7 towards oxidation parallels the photochemical reactivity of 4. The hyperfine coupling constants of the radical cations derived from 6 and 7 indicate that the removal of an electron is accompanied by an isomerization of the molecular framework. The investigation of the electron transfer process gby cyclic voltammetry supports these findings. The radical cations prefer the cyclophane-like structures 6a and 7a, in which the central σ-bond (C(15)-C(16) bond) is broken.
    Additional Material: 7 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19840670302
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  • 25
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    Photochemistry of 2-(Trifluoromethyl) cyclohexanone (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 664-668 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The photochemical behaviour of the title compound 1a is compared to that of the non-fluorinated parent ketone 2-methylcyclohexanone (1b). Substitution of the CH3- group on C(2) by a trifluoromethyl group strongly enhances 2H- and RH- reduction product formation in cyclohexane or 2-propanol and oxetane formation in the presence of 2-methylpropene as olefinic component. Under all these conditions 1b exclusively undergoes a-cleavage, a process observed for 1a only in non-reducing solvents as benzene or tert-butyl alcohol.
    Additional Material: 2 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19840670305
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  • 26
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    Synthesis of Optically Pure Compounds by Enantiotopically Differentiating Monoacetalization of Prochiral Diketones. Part II. Fragmentation of β-Keto-AcetalsPart I: [1]. These results, which have been presented in part at the ‘Herbstversammlung der Schweizerischen Chemischen Gesellschaft’, October 16, 1981, in Bern, are comprised in the Ph. D. thesis of P. M. [2]. The nomenclature and classification of stereodifferentiating reactions proposed by Izumi & Tai [3] are used in this communication (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 832-844 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Treatment of β-keto-acetals, derived from non-enolisable β-diketones, with sulfonic acids in boiling benzene resuots in a smooth retro-Claisen-type fragmentation. The acetal-C-atom is thereby transformed into a carboxylic ester via a dialkoxycarbenium ion, which is dealkylated by the sulfonate counter-ion. Application of this reaction to the diastereomeric monoacetals 3 and 4, derived from cis-9-methyl-decalin-1,8-dione (1), followed by transesterification with CH3OH, yields optically pure 4-(2′-methyl-3′-oxocyclohexyl)butyrate 9 ((+)-9 from 3, (-)-9 from 4) and the monosulfonate of Meso-2,3-butanediol (-)-13 (Scheme 2). Unexpectedly, this cleavage proceeds as well with monoacetal 26, obtained by acetalization of trans-9-methyl-decalin-1,8-dione (27) with 2,2-dimethyl-1,3-propanediol (Scheme 7). Some attempts, aiming at an isomerization of the cis- and trans-decalin derivatives 3 and 24, or 25 and 26, via the postulated carboxonium intermediate, were not successful.
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    URL: http://dx.doi.org/10.1002/hlca.19840670324
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  • 27
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    Preparation of Bicyclo[3.3.0]octane-2,8-dione- and Declain-1,8-dione-DerivativesThese results are comprised in the Ph. D. thesis of P. M. [1] (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 856-865 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Alkylation of bicyclo[3.3.0]octane-2,8-dione (1), which is prepared by a modification of the procedure described in the literature, gives the methyl- and propynyl-derivatives 6 and 7 (Scheme 1). In addition to the method described previously (Scheme 2), 9-methyl-cis-decalin-1,8-dione 9 is obtainable stereoselectively either by cyclization of keto-acid 16, or by aldol cyclization of keto-aldehyde 26 and oxydation of the resulting alcohols 24 and 25 (Scheme 4). The β-keto-alcohols 24 and 25 undergo a base-catalyzed isomerization; the trans-decalin isomers 27 and 28 are not detected in this equilibrium mixture (Schemes 4 and 5)l. Monoreduction of cis-dione 9 gives the endo-alcohol 25, while 27 is the favored product of the reductin of trans-dione 10 (Scheme 4). Optically pure (+)-25 can be prepared from (9S,10R)-monoacetal 29 (Scheme 5).
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    URL: http://dx.doi.org/10.1002/hlca.19840670326
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  • 28
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    Synthesis of a S-(Carboxymethyl)cysteine Analog of (L-2-Amino-6-adipyl)-L-cysteinyl-D-valine and its Cell Free Biosynthetic Conversion into 6-[2-(D-2-Amino-2-carboxyethyl)thio) acetamido]penicillanic Acid (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 870-875 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new tripeptide (dimer), bis[(L-cysteine-S-acetyl)-L-hemicystinyl(S2 → S2)-D-valine] (6) was synthesized by coupling N-(tert-butoxycarbonyl)-S-carboxymethyl-L-cysteine benzyl ester (1) with S-trityl-L-cysteinyl-D-valine benzyl ester and subsequent removal of the protecting groups. After reduction of the disulfide, the free tripeptide Cys (CH2CO-Cys-D-Val) (Ib) was used as a substrate of isopenicillin-N synthetase in a cell-free conversion to 6-[2-((D-2-amino-2-carboxyethyl)thio)acetamido]penicillanic acid (IIa).
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19840670328
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  • 29
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    The Synthesis of cis- and trans- 7-Phenylkacetamido-O-2-isocephemO-2-Isocephems are alternatively called isooxacephems (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 902-905 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the title compounds is described.
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    URL: http://dx.doi.org/10.1002/hlca.19840670331
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    Erratum (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 927-927 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670334
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  • 31
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    Absolute Conformation and Configuration of (2S, 3S)-3-Acetoxy-5-(dimethylaminoethyl)-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one Chloride (Dilthiazem Hydrochloride) (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 916-926 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Resolution of racemic cis-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl) propionic acid (2) via the cinchonidine salt 3, and brucine salt 4, isolation of the calcium salts (+)- and (-)-5, as well as their cyclization to enantiomeric 1,5-benzothiazepines (+)- and (-)-1, are described. X-Ray single-crystal analysis reveals (2S, 3S) absolute configuration of (+)-1 on the basis of tentative comparison of CD data with those for the 1,4-benzodiazepine derivative (+)-8 of known absolute configuration.
    Additional Material: 4 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19840670333
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    Masthead (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984) 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670401
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  • 33
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    Synthese und Struktur von Zink-Komplexen von 2-Amino-1-azetinen (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 927-933 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis ad Structure of Zinc Complexes of 2-Amino-1-azetinesThe 2-dimethylamino-3,3-dimethyl-1-azetines 7a and 7b have been synthesized in analogy to the procedure reported by Ghosez et al. [1] (Scheme). The crystal structure of 1-benzhydryl-azetidindimethyliminium chloride 5a, a precursor of azetine 7a, has been established by X-ray diffraction analysis. Treatment of azetines 7a and 7b with ZnBr2 in CH2Cl2/MeCN yielded tetrahedral bis (azetine)dibromozinc complexes 8a and 8b, respectively (Scheme 2). The molecular structure of 8a has been determined by X-ray diffraction analysis too.
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  • 34
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    Enantioselective synthesis of (+)- and (-)-cis-2-methyl-4-propyl-1,3-oxathiane and their olfactive properties (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 947-952 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantioselective synthesis of (+)- and (-)-cis-2-methyl-4-propyl-1,3-oxathine 8 and 9 form (E)-2-hezen-1-ol (1) as common starting material is described. The two enantiomeric forms exhibit different organoleptic properties.
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    Aliphatic Liquid Crystals with Positive Dielectric Anisotropy (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 959-963 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cyanothyl-subsituted cylohexyl cyclohexanoates, bi(cyclohexanes) and phenyl cyclohexanes were synthisized. Their mesmorphic behaviour is compared to that of the corresponding cyano derivatives. (Cyanoethyl)cyclohexyl cyclohenxanoates show mesmorphic properties in contrast to the corresponding cyano derivative. Separation of the cyano substituent from the rigid core of an anisotropic aliphatic compound by methylene groups enhances the thermodynamic stability of the mesophase. In aromatic compound, the cyanoethyl group leads to lower clearing points. These phenomena are attributed to teh influence of steric effects on the packing density and to the dependence of the clearing point on molecular association.
    Additional Material: 2 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19840670407
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  • 36
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    Monohaptenic Nα-Benzoyl-L-lysine Derivatives as Anaphylactogens: the Importance of the Unsubstituted Carboxyl Group (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1000-1002 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Nα-L-Iysine with a 2-carboxy-4, 6-dinitrophenyl (Dncp) haptenic group on the ε-amino function is a potent anaphylactogen in the guinea pig. We prepared Nε -Dncp- Nα-benzoly-L-Iysinamide and Nε-Dncp-Nα-benzoyl-L-lysyl-1-aminopropane where the carboxyl group of Iysine is blocked. Both compounds were non-elections of anaphylaxis.
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    URL: http://dx.doi.org/10.1002/hlca.19840670411
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  • 37
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    C45- und C50-Carotinoide. 2. Mitteilung. Synthese von optisch aktiven acyclischen C15-Endgruppen (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 21-28 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: C45- and C50-Carotenoids. Synthesis of Optically Active Acyclic C15-End GroupsThe optically active C15-end groups (S)-12, (S)-13 and (R)-14 were prepared from the C12-synthon (S)-11 in good chemical and optical yield. These C15-end groups are suitable compounds for the synthesis of optically active C45- and C50-carotenoids.
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  • 38
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    Interactions between Functional Groups. Part I. Crystal Structure of 2-Phenylethynyl-N,N-dimthlaniline at 98 K: A Remarkably Short C—H … C Distance (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 39-46 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In the crystal structure of the title compound at 98 K the dimethylamino group has pyramidal geometry. The nitrogenlone pair is not directed towards the triple bond; instead, one N—CH3 bond lies almost in the plane of the disubstituted ring, directed away from the triple bond, while the other N—CH3 bond and the lone pair are directed to opposite sides of the plane, nearer to the acetylene. There is a remarkably short intramolecular contact (2.39 Å) between a methyl H- and an acetylenic C-atom. The Taft σI parameter of the arylethynyl substituent appears to be similar to that of a carboxylic ester, judging from the bond-angle deformation at the ipso-C-atom.
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  • 39
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    Die Herzglykoside des Pfeilgiftes von Lophopetalum toxicum LOHER. 13. Mitteilung über Celastraceen-InhaltsstoffeAus der Dissertation von Helmut Habermeier, München, 1981. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 54-64 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Heart Glycosides of the Arrow Poison of Lophopetalum toxicum LOHERFrom the cytotoxic and positive inotropic acting bark extract of the Philippinan Lophopetalum toxicum eight heart glycosides have been isolated and their structures have been elucidated mainly by field-desorption-MS- and 1- and 13C-NMR spectroscopy. Besides the known k-Strophanthidin (1), Antiarigenin (6) and β-Antiarin (Antiarigenin-3-β-O-α-L-rhamnoside, 10) the following mono- and diglycosides could be identified: strophanthidin-3-β-O-α-6-desoxy-D-allopyranoside (strophalloside, 2), strophanthidin-3-β-O-β-6-desoxy-D-glucopyranoside (= Strophanthidin chinovoside, 3), strophanthidin-3-β-O[-4Oβ-D-allopyranosyl-β-6-desoxy-D-allopyranoside] (4), strophanthidin-3-β-O-[3-O-β-D-glucopyranosyl-β-6-desoxy-D-talopyranoside] (5), antiarigenin-3-β-O-[3-O-β-D-gulopyranosyl-β-6-desoxy-D-talopyranoside] (7), antiarigenin-3-β-O-[4O-β-D-allopyranosyl-β-6-desoxy-D-allopyranoside] (8), and antiarigenin-3-β-O-β-6-desoxy-D-allopyranoside (antiallosid) (9). The structure of strophanthidinchinovoside (3) could be confirmed by synthesis.
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    On the Structure of Oxirane Molecular Cation. Preliminary CommunicationDedicated to Prof. Christoph Tamm on the occasion of his 60th birthday (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 86-90 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A recent controversy on the interpretation of the ESR spectrum of ionized oxirane is clarified on the basis of the electronic absorption spectra of ionized tetramethyloxirane and 9,10-octalineoxide. The results favour a ring-opened structure for oxirane molecular cation, resulting from C—C bond cleavage and being iso-π-electronic to allyl radical.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19840670111
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  • 41
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    Die Acylierung von Acetylenen mit β, γ-ungesättigten Säurechloriden. Eine neue Synthese von 5-CyclopentenonenTeilweise vorgetragen an der Versammlung der Schweizerischen Chemischen Gesellschaft am 15. Oktober 1982 in Bern; als vorläufige Mitteilung erschienen in [1]. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 73-85 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Acylation of Acetylenes with β,γ-Unsaturated Acid Chlorides, A New Synthesis of 5-Substituted 2-CyclopentenonesThe acylation of acetylenes with α,α-disubstituted, β,γ-unsaturated acid chlorides under Friedel-Crafts-type conditions leads to 5-substituted 2-cyclopentenones. Phenols are formed with β,γ-unsaturated acid chlorides bearing at least one α-H-atom. These transformations are explained by the intramolecular cyclization of the initially formed vinyl cation, which, in the cases of α,α-disubstituted acid chlorides, is followed by ring contraction. The reaction leading to 2-cyclopentenones is applied to the synthesis of some spiro[4.4]nona- and spiro[4.5]deca-2,6-dienones.
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  • 42
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    Palladium-promoted Cyclization of Tetra-alkylated 1-Arylazonaphthalenes to 2-Aryl-benzo[g]indazoles (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 113-119 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1-Arylazonaphthalenes with all the potential cyclopalladation sites (one peri- and three ortho-positions) substituted by methyl or ethyl groups react with stoicheiometric or catalytic amounts of sodium tetrachloropalladate(II) to the corresponding 2-arylbenzo[g]indazoles. Possible mechanisms for the catalytic cyclization reaction are proposed.
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  • 43
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    Photochemical reactions. 132nd communication131st Communication, see [1]. Photochemistry of 5,6-epoxy-5,6-dihydro-7-methyl-β-ionine: Influence of a methyl group at the enone side chain on the oxirane cleavagePresented in Part by B. F. at the IXth IUPAC Symposium on Photochemistry, July 25-30 1982, Pau (France). (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 120-128 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1n, π*-Excitation of the γ,δ-epoxy-enone (E)-3 leads exclusively to the conformers (Z)-3A + B. On 1π, π*-excitation of (E)-3, in addition to (Z)-3A + B, products 6-9 arising from a carbene intermediate e are formed. However, products of an isomerization via C(γ), O-bond cleavage of the oxirane were not formed on either mode of excitation. On thermolysis, at 80° the conformer (Z)-3A is transformed into (Z)-3B, which on photolysis returns to (Z)-3A and (E)-3. At 160°, however, (Z)-3B rearranges to the isomers 6, 10 and 11.
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  • 44
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    Selective Photoinduced Oxidation of Benzylic Methylen Groups through UV Irradiation in Presence of Ferric Chloride (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 866-869 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Selective oxidation of benzylic methylene groups through UV irradiation in acetone/water/FeCl3 mixtures is reported. This method applied to a series of model compounds, provides an easy access to the corresponding 1-oxo derivative. Thus, tetralin gives a 100% yield of 1-tetralone, indane leads to 60% of 1-indanone, and diphenylmethane is oxidized to benzophenone with 80% yield. However, under the same conditions, alkyl-substituted aromatic hydrocarbons such as toluene, ethyl- and propylbenzene lead to low yields of aldehydes or ketones. Isochromane furnishes a mixture of two substances which can be interconverted, namely the expected l-isochromanone (9%) and the corresponding hydroxy acid (23%). We failed to apply the method to nitrogen heterocycles containing benzylic groups such as 1,2,3,4- and 5,6,7,8-tetrahydroquinoline as they do not react due to the formation of complexes which precipitate from the solutions.
    Additional Material: 1 Tab.
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  • 45
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    High performance liquid chromatography (HPLC) of natural products part VI.For part V, see [1] Sulfoxides of penicillin N and cephalosporin c and their role in biosynthesis of β-lactam antibiotics (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 876-884 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pure pencillin N α-sulfoxide (1) and penicillin N β-sulfoxide (2) were obtained by HPLC and tested as substrates for deacetoxycephalosporin C synthetase (DXCS). Neither one of the sulfoxides was utilized under conditions of conversion of penicillin N (8) to deacetoxycephalosporin C (9). The cephalosporin C α and β-sulfoxides (3 and 4, resp.) were also prepared. Relative stabilities of the sulfoxides 3 and 4 are discussed by interpretation of the 13C-NMR spectra.
    Additional Material: 9 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19840670329
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  • 46
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    Die Busseine C, D, E, F, G, H, J, K, L und M, zehn neue Tetranortriterpene aus Entandrophragma bussei Harms.Herrn Prof. D.A.H. Taylor, University of Natal, Durban, Natal, South Africa, danken wir bestens für die Überlassung von Extrakten. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 885-901 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Business C,D,E,F,G,H,J,K,L und M, Ten New Tetranortriterpenes from Entandrophragma Bussei HarmsTen new tetranortriterpenes, busseins C, D, E, F, G., H, J, K, L and M have been isolated from the petroleum ether extract of the timber of Entandrophragma bussei Harms. utilizing separation by high-pressure liquid chromatography (HPLC). The structural assignments are based mainly on spectral evidence. For the 1H-NMR spectroscopy extensive use of nuclear Overhauser effects (NOE) was made.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19840670330
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  • 47
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    Mitteilungen-Communiacations (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 928-930 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670335
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    The Synthesis and Application of Novel Nitrating and Nitrosating AgentsWork supported by the Shiraz University Research Council. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 906-915 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Alcohols and phenols are efficiently nitrated with thionyl chloride nitrate or thionyl nitrate, even in the presence of an aromatic moiety. While thionyl chloride nitrate is suitable for nitration of primary OH-groups in carbohydrates, thionyl nitrate is reactive enough to react with secondary OH-groups as well. These reagents permit the highly selective nitration of the 5′-,2′5′- and 3′, 5′-OH-groups of ribonucleosides to produce either mono-or diprotected nitro derivatives in high yields. Carbon acids and the enol form of some ketones are efficiently nitrated with trifluoromethanesulfonyl nitrate/potassium tert-butoxide. Lutidine N-oxide (2,6-(CH3)2C5H3N O) was found to have a marked effect on nitration reactions. Similarly, thionyl chloride nitrite and thionyl nitrite exhibit an excellent capacity for nitrosation of the aforementioned substrates.
    Additional Material: 5 Tab.
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    Radical Ions of Conjugated Polycyclic Hydrocarbons Containing Two Phenalenyl π-Systems (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 934-938 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The radical cations and the radical of 1,2-bis(phenalen-1-ylidene)ethane (1), 1,2-bis(phenalen-1-ylidene)ethene (2) and pentaleno[1,2,3-cd: 4,5,6-c′ d′]diphenalene (3) have been characterized by ESR and ENDOR spectroscopy. The ease of formation of these radical ions and their π-spin distributions are interpreted in terms of a simple model correlates the frontier orbitals of 1, 2 and 3 with the nonbonding MO's of two phenalenyl π-systems.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19840670403
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    The Synthesis and Reactions of 1-(2-Propynyl)pyidinium Salts (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 939-946 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of 1-(2-propynyl)pyridinium salts 3 described. Compounds 3 react with a second pyridine molecule, in the presence of the corresponding hydrochloride, to form products of type 4, Certain bases cause the 1-(2-propynyl)pyridinium salts 3 to rearrange into 1-propadienylpyridinium salts. 5. Diethylamine converts compounds 3 into 1-acetonylpyridinium salts 8. Moreover, treatment of 3 or 5 with sodium methoxide gives enol ether sof type 9, which can be hydrolyzed to teh ketones 8. Addition of bromine to some of teh unsaturated compounds is also reported.
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    URL: http://dx.doi.org/10.1002/hlca.19840670404
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    HNO, an Intermediate in (Light-induced) Rearrangement Reactions of Nitrosooxy Compounds and Nitrosamines (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 953-958 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: IR-spectroscopic investigations of light-induced rearrangement reactions of nitrosooxymethane (CH3ONO3), nitrosooxyethane (CH3CH2ONO) and N,N-dimethylnitrosamine ((CH3)2NNO) in low-temperature rare-gas matrices have established that these molecules are transformed in two photolysis steps to the previously unknown C-nitroso compounds nitrosomethanol (CH2(OH)(NO)), 1-nitrosoethanol (CH3CH(OH)(NO)), and methyl(nitrosomethyl)amine CH2(NO)(NH)(CH3). Evidence for a similar rearrangement reaction has been advanced for N-Nitrosopyrrolidine which is converted to C-nitrosopyrrolidine . The matrix-isolation technique in combination with wavelength-selective irradiation allowed to trap and characterize an intermediate of rearrangement which revealed to be nitroxyl (HNO) complex (CH2…HNO, CH3CHO…HNO, CH3N = CH2…HNO, and ). Since these findings have a close resemblance with rearrangement reactions of more complex nitrosooxy compounds, nitrosamines, or nitrosohydrazines used in organic synthesis, it is suggested that also in these reactions nitroxyl is present as an intermediate species.
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    1,2-Epoxycarotinoide. 3. Mitteilung. Isolierun von 1,2-Epoxy-1,2-dihydrolycopin aus Tomaten (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 964-967 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,2-Epoxycarotenoids: Isolation of 1,2-Epoxy-1,2-dihydrolycopene from TomatoesThe optically active, 1,2-epoxy-1,2-dihydrolycopene was isolated from tomatoes. Its constitution was established by comparison with the racemic synthetic compound.
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    1,2-Epoxycarotinoide. 4. Mitteilung. Synthese, 1H-NMR- und CD-Studien von (S)-1,2-Epoxy-1,2-dihydrolycopin und (S)-1′,2′-Epoxy-1′,2′-dihydro-γ-carotin (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 968-985 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,2-Epoxycarotenoids: Synthesis, 1H-NMR and CD Studies of (S)-1,2-Epoxy-1,2-dihydrolycopene and (S)-1′,2′-Epoxy-1′, 2′ -dihydro-γ-caroteneThe synthesis of (S)-1,2-epoxy-1,2-dihydrolycopene ((S)-1) and (S)-1′, 2′ -epoxy- 1′, 2′ -dihydro-γ-carotene ((S)-2) are described. The CD spectra of the (all-E)-isomers and of the isomers (7Z, S)-1 and (7′Z, S)-2 are discussed. The comparison of the CD spectra of the synthetic (S)-1 and the compound isolated from the tomatoes proves the (S)-configuration of the natural product.
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    Plectranthone A, B, C und D. Diterpenoide Phenanthren-1,4-dione aus Blattdrüsen einer Plectranthuus sp. (Labiatae) (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1003-1011 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Plectranthons A, B, C, and D. Diterpenoid Phenanthrene-1,4-diones from Leaf-glands a Plectranthus sp. (Labiatae)The following structures of four new 1,4-phenanthraquionones, isolated in minute amounts from the coloured leaf-glands of a Plectranthus sp. obtained from the borders of Lake Kiwu2, Rwanda, are proposed: plectranthon A (1; 3-hydroxy-5, 7,8-trimethyl-2-(2-propenyl)phenanthrene-1, 4-dione), plectranthon B (2; 2-(2ξ-acetoxypropyl)-3-hydroxy-5,7,8-trimethylphenanthrene-1,4-dione), plextranthon C (3; 3-hydroxy- 7,8-diemethyl-2-(2-propenyl)phenanthrene-1,4-dione), and plectranthon D (4; 3-hydroxy-7,8,10-trimethyl-2-(2-propenyl)phenanthrene-1,4-dione). 2-(2ξ-Hydroxypropyl)-3,6-dihydroxy-5,7,8-trimethylphenanthrene-1,4-dione (11), a compound very similar to 1-4, was prepared by a Wagner-Meerwein, rearrangement of coleon E (5). Biogenetically, the plectranthons are derived from abietanoic precursors. The compounds 1, 2 and 4 are the first natural C20-phenanthrenes of diterpenoid origin.
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    Stereoselective Control in the Base-Catalyzed H/D Exchange of 5,6-Dimethylidene-2-bicyclo[2.2.n]alkanone Tricarbonyliron Complexes. Revision of the Structures of Tricarbonyliron Complexes of 5,6-Dimethylidenebicyclo[2.2.2]oct-2-ene and 5,6-Dimethylidenebicyclo[2.2.1]hept-2-eneA preliminary communication was presented at the Autumn Meeting of the Swiss Chemical Society, Bern, October 14, 1983. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 986-999 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oxidative hydroboration of exo- (1) and end-Fe(CO)3 (2) complexes of 5,6-dimethylidenebicyclo[2.2.2]oct-2-ene are highly stereoselective and give endo -alcohol 3 and exo -alcohol 4 as major products, respectively, Collins oxidations of 3 and 4 furnish the corresponding exo -Fe(CO)3 -complexed 5,6-dimethylidene-2-bicyclo-[2.2.2]octanone 7 and 8. NaBH4 reduction of exo-complexes 7 gives a mixture of 3 and isomeric exo-alcohol 18, whereas reduction of endo-complexes 8 gives the endo-alcohol, endo-complexes 19, as the sole product. The base-catalyzed H/D exchange of 7 and 8 afford the dideuterated exo-complex 35 and the monodeuterated endo-complex 32, respectively. Oxidative hydroborations of the exo-(9) and endo-Fe(CO)3 (10) complexes of 5,6-dimethylidenebicyclo[2.2.1]hept-2-ene give the corresponding exo-alcohols 39 and 40. Oxidation of 39 and 40 gives the exo- and endo-complexes 41 and 42, respectively, of 5,6-dimethylidene-2-bicyclo[2.2.]heptanone. Only Hexo —C(3) can be exchanged in 42, wheres both H-atoms at C(3) in 41 are exchangeable. The endo-Fe(CO)3 group in 8 and 42 blocks the base-catalyzed H/D exchange of Hendo —C(3), thus providing a test for the configuration of Fe(CO)3 group in these systems. These studies have led to a revision of the iron configurations proposed by Hansen et al, [2] for 1, 2, 9 and 10.
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    Mitteilungen - Communications (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 361-364 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670143
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    Parallelism Between Nucleophilically Solvent-Assisted and Phenyl-Assisted Reactions. Possible Existence of Nucleophilically β-Phenyl-Solvated Ion Pairs (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 352-360 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Solvolysis rate constants in MeOH and t-BuOh are compared for β-methyl and β-phenyl derivatives of two cycloakyl systems. It appears that the β-phenyl derivatives solvolyse at te same rate as the β-methyl ones. The lack of deceleration is attributed to phenyl assistance. It is established by configurational analysis of the reaction products, that those products which necessarily originate from a cationic species are the most abundant ones. It is suggested that these reactions could proceed through ion-pair intermediates, which are nucleophilically solvated by phelyl or by the solvent. A parallel between phenyl assistance and ‘SN2 (intermediate)’ mechanism, suggested by Bentely & Schleyer, is drawn.
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    Percolative Phenomena in Microemulsions of the ‘One-Component Macrofluid’ Type (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 361-372 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The temperature dependence of the water self-diffusion coefficients (D), as well as those of low- and high-field (stationary and time-dependent) specific conductivities (K), have been determined in the percolation regime of ternary mixtures of water, AOT, and oil. For the first time a pronounced similarity in the behavior of D and κ was detected giving instructive hints about the large variations in the specific conductivities of these systems. Results from kinetic and stationary experiments are consistent with a network-structure model of micro phases in the percolation regime in which the micro phases retain their discrete character.
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    URL: http://dx.doi.org/10.1002/hlca.19840670202
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    Synthèse facile de dérivés du diphényl-2,4-aza-3-bicyclo[3.3.1]nonane et du diphényl-7,8-aza-8-bicyclo[4.3.1]décaneUne partie de ce travail a fait l'object d'une communication préliminaire [1]. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1291-1297 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Facile synthesis of derivatives of 2,4-diphenyl-3-azabicyclo[3.3.1]nonane and 7,9-diphenyl-8-azabicyclo[4.3.1]decaneThe facile synthesis of hydantoins, cyanhydrins and aminonitriles derived from 2,4-diphenyl-3-azabicyclo[3.3.1]nonanone and 7,9-diphenyl-8-azabicyclo[4.3.1]decanone is described. Configurations at C(9) or C(10) of the new compounds wth pharmaceutical and synthetical utility is deduced from their spectral properties.
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    Fragmentation of 6-Deoxy-6-halo-hexono-1,5-ortholactones: A Concerted, Nonstereospecific Process (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1328-1347 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the D-arabino- and D-ribo-ortholactones 13a-f and 15b-f and their treatment with Zn leading to the unsaturated esters 14a-d and 16a-d are described. Possible fragmentation mechanisms are discussed. The results were only compatible wit a concerted, nonsynchronous process, where both the axial lone pair of the ring oxygen atom and the lone pair formed during rupture of the C(5), O-bond participate in the elimination of the axial and of the equatorial C(1)-alkoxy groups, respectively.
    Additional Material: 4 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19840670519
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    Electron-Transfer-Induced Conformational Changes. The Example of 1,8-Dimethyl[14]annulene (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1368-1373 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: This communication reports ESR-spectroscopic investigations of the radical anion of 1,8-dimethyl[14]annulene (1) which possesses a flexible molecular framework allowing configurational and conformational mobility. The ESR and ENDOR spectra indicate that at higher temperatures (T 〉 160 K), \documentclass{article}\pagestyle{empty}\begin{document}$ 1^{- \atop \dot{}} $\end{document} exists as a mixture of several distinct isomers. One of them, the sole product at T 〈 160 K, is found to be energetically preferred. The configuration and the conformation of this species can be determined by interpretation of the hyperfine data in terms of a singly occupied MO of the 14-membered π-perimeter.
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    Dimers of 3,7-dehydrotroponesFor this nomenclature, see [1a]. (bicyclo[3.2.0]hepta-1(7),2,4-trien-6-ones) (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1386-1396 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-(tert-Butyl)-3,7-dehydrotropone (7-(tert-butyl)bicyclo[3.2.0]hepta-1(7),2,4-trien-6-one; 1) was found to dimerize reversibly to 2A by [2 + 4]-cycloaddition/cycloreversion reaction. The equilibrium lies on the side of the highly strained dimer 2A in the solid state, and on the side of the monomer 1 in solution. The [2 + 4]-reaction is fully perisite-, regio- and stereoselective. Above room temperature, 1 irreversibly formed a decarbonylated dimer 6, probably via the intermediate 9A or 9B, which resulted either from a dimerisation of 1 by [4 + 6]-cycloaddition or from a sigmatropic rearrangement of the originally formed dimer 2A or 2B. Similary, the 6-bromo derivative 14 afforded the corresponding decarbonylated dimer 15. Should the formation of 6 and 15 be due to a primary cycloaddition then that reaction is fully peri-, site- and regioselective. Mild LiAlH4-reduction of 6 and subsequent acetylation yielded the acetate 11, the structure of which was established by an X-ray analysis. More vigorous LiAlH4-treatment also reduced the terminal fulvenoid double bond of 6 and acetylation of the crude product led to the acetated 12 and 13.
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    Mitteilungen - Communications (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1427-1428 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670530
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    Elektromotorisches Verhalten von Flüssigmembranelektroden-Messketten mit enantiomerenselektiven chiralen Ionophoren (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1427-1438 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Electromotive Behaviour of Liquid-membrane Electrode Assemblies Based on Enantiomer-selective Chiral IonophoresA comprehensive theoretical treatment is given for the potentiometric behavior of enantiomer-selective membrane electrodes based on chiral ionophores and plasticizers. The membrane model allows for free and complexed enantiomeric or racemic ions (e.g. ephedronium and l-phenylethylammonium ions) as well as for achiral interfering ions. Experiments are derived for the determination of the stoichiometry and the relative stability of enantiomeric ion/enantiomeric ligand complexes, and for the analytical measurement of the enantiomeric excess of ions in solution.
    Additional Material: 5 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19840670602
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    Water-Exchange Mechanism of Tetraaquapalladium(II). A Variable-Pressure and Variable-Temperature Oxygen-17 NMR StudyPart 23 of the series ‘High-Pressure NMR Kinetics’. For part 22, see [1]. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1453-1460 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Water exchange of square-planar Pd(H2O)24+ has been studied as a function of temperature (240 to 345 K) and pressure (0.1 to 260 MPa, at 324 K) by measuring the 17/O-FT-NMR line-widths of the resonance from coordinated water at 27.11 and 48.78 MHz. The following exchange parameters were obtained: k298ex = (560 ± 40) s-1, ΔH* = (49.5 ± 1.9) kJ mol-1, ΔS* = - (26 ± 6) J K-1 mol-1 and ΔV* = - (2.2 ± 0.2) cm3 mol-1. The values refere to an aqueous perchlorate medium with an ionic strength between 2.0 and 2.6 m and a perchloric-acid concentration between 0.8 and 1.7 m, and are interpreted in terms of an associative (a) activation for the exchange. The exchange rate for Pd(H2O)24+ is 1.4 × 106 times faster than for Pt(H2O)24+ at 298 K. A comparison with reactions between other nucleophiles and Pd(H2O)24+ is also made.
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    Etudes sur les composés organométalliques partie XXPartie XIX, v. [5]. Sélectivité de l'addition 1,4 de composés benzyliques du titane IV avec la benzylidéneacétone (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1475-1477 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Studies of Organometallic Compounds, XX. Selectivity of 1,4-Addition of Benzyltitanium Compounds with BenzylildenacetoneTetrabenzyltitanium and dialkoxydibenzyltitanium compounds give essentially 1,4- addition with trans-4-phenyl-3-buten-2-one.
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    Aminierende, reduktive Kupplung aromatischer Aldehyde mit Tris(dialkylamino)methylvanandium (IV) zu N,N,N′,N′-Tetraaalkyl-1,2-diaryläthylendiaminen (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1496-1502 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Aminative Reductive Coupling of Aromatic Aldehydes to N,N,N′,N′-Tetraalkyl-1,2-diarylethylenediamines, Induced by Tris(dialkylamino)methylvanadium (IV)In a novel type of reaction, certain aromatic aldehydes (benzaldehyde, p-methoxybenzaldehyde, 1-naphthaldehyde, furan-2-carbaldehyde) and secondary amines are coupled to give N,N,N′,N′-tetraalkyl-1,2-diarylethylenediamines 1-6. The reagents are tris(dialkylamino)methylvanadium(IV) compounds (cf. Eqn. 2). These are generated in situ either from isolable chlorotris(dialkylamino) vanadium(IV) (Eqn. 3), or preferably, from an Et2O/pentane solution of VCl4 which is treated sequentially with 3 equiv. of lithium dialkylamide, 1 equiv. of MeLi, and 0.8 equiv. of an aromatic aldehyde, to give the products 1-6 in a one-pot preparation (Scheme 2). The yields range from 14 to 54%. The diastereoisomeric mixtures (meso- and (±)-forms) obtained are separated by chromatography (Al2O3, petroleum ether/Et2O/Et3N), and the pure stereoisomers fully characterized. A mechanism of the reductive coupling induced by CH3V (NR2)3 is proposed (Scheme 1).
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    Functionalized Cycloheptanes from Bicyclo[4.2.1]nonanes (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1506-1514 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Several oxidative, reductive and C,C-cleavage reactions were performed starting from the three bicyclo[4.2.1]nona-3,7-diene-2-one derivatives 1, 5 and 18. The oxidations were selective and led to the diols 2,8 and 9, and the epoxides 6,9, and 20. The reductions were selective only in the case of 20 21; otherwise they led to mixtures of the alcohols 10 and 11, and of the dienes 14 and 15. The periodate ring cleavages afforded the functionalized cycloheptane derivatives 3, 12, 13 and 16. Configurational assignments were made on the basis of detailed 1H-NMR and X-ray analysis of 20.
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    Drüsenfarbstoffe aus tropischen Labiaten: Parviflorone aus Plectranthus strigosus BENTH. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1531-1534 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Red-Coloured Abietanoids from Leaf-Glands of Plectranthus strigosus BENTH.Chromatographic examination of the red-coloured diterpenoids from the South-African title plant yielded the following compounds: parviflorone A(1), parviflorone B (2), parviflorone C(3), parviflorone E (4) parviflorone D (5), parviflorone F (6), parviflorone G (7), and parviflorone H (8). Compounds 7 and 8 represent new variants of these quinone methides.
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    URL: http://dx.doi.org/10.1002/hlca.19840670617
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    Drüsenfarbstoffe aus Labiaten: Die polaren Diterpenoide aus Plectranthus argentatus S. T. BLAKEVorangehende Arbeiten s. [1] [2] und darin zitierte frühere Publikationen. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1523-1530 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Polar Diterpenoids from Leaf-Glands of Plectranthus argentatus S. T. BLAKEFrom the red leaf-glands of the Australian Plectranthus argentatus the following novel diterpenoids were isolated: coleon-U-quinone (1), 8α,9α-epoxycoleon-U-quinone (3), 6β-formyloxy-7α-hydroxyroyleanone (7), and 5,6-dihydrocoleon U (10), besides the already known compounds 6β, 7α-dihydroxyroyleanone (4), 7α-acetoxy-6β-hydroxyroyleanone (5), and 7α-formyloxy-6β-hydroxyroyleanone (6). Epoxydation of 1 by perborate led in 32% yield to the epoxyquinone 3.
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    Deoxy-nitrosugars 8th communication7th Communication: [1]. Convenient preparation of 1-C-nitroglycosyl chlorides. Halonitro ethers from hydroxy oximes (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1568-1571 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Partially protected 4- or 5-hydroxy-sugar oximes were transformed into 5- or 6-membered 1-C-nitroglycosyl chlorides, respectively, by reaction with NaOCl under phase-transfer conditions. With the exception of the oxidation of the gluco-derivative 1 giving the anomers 6 and 7, the reactions were completely diastereoselective.
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    The synthesis and transition temperatures of benzoate ester derivatives of 2-fluoro-4-hydroxy-and 3-fluoro-4-hydroxybenzonitriles (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1572-1579 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis and the liquid-crystal temperatures of sixty 4-cyano-2-fluorophenyl and 4-cyano-3-fluorophylen 4-substituted benzoates are described. The nematic-isotropic liquid transition temperatures of the most of these novel esters are only marginally lower than those of the corresponding esters containing an H-atom in place of the F-substituent. In several instances, the clearing points of the F-substiuted-phenyl esters are higher than those of the non-substituted-phenyl esters. The nematic ranges of several of the new esters are markedly broader than those of the analogous non-F-substituted-phenyl esters.
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    URL: http://dx.doi.org/10.1002/hlca.19840670623
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    An Example of Head-to-Head Dimerization of β4.4-Helices (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1588-1592 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1H-NMR and vapor-pressure osmometry results are presented, which indicate the occurrence of a rapid equilibrium involving the head-to-head dimerization of β44-helices in chloroform solutions of HCO-L-Ile-(D-AIle-L-Ile)4-OMe. This equilibrium typifies the one that, in Urry's view, would be responsible for the formation and breaking down of the ion-conducting channels formed by gramicidin A in lipid bilayers.
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    URL: http://dx.doi.org/10.1002/hlca.19840670625
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    The synthesis and transition temperatures of ester derivatives of 2-fluoro-4-hydroxy- and 3-fluoro-4-hydroxybenzonitriles also incorporating aliphatic ring systems (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1580-1587 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis and liquid-crystal transition temperatures of forty ester derivatives of 2-fluoro-4-hydroxybenzonitrile and 3-fluoro-4-hydroxybenzonitrile are reported. The esters contain the trans-1,4-disubstituted cyclohexane or the 1,4-disubstituted bicyclo[2.2.2]octane rings (some contain an additional phenyl ring). Many of the novel F-substituted esters exhibit substantially higher nematic-isotropic transition temperatures than the corresponding unsubstituted esters. The order of clearing points of these laterally substiuted esters differing only in the presence of a benzene ring and the above-mentioned rings id established.
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    URL: http://dx.doi.org/10.1002/hlca.19840670624
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    Synthese von neuen Morphin-Teilstrukturen des Typs 15,16-Secomorphinan (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1598-1602 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of New Morphine Partial Structure 15,16-SecomorphinanThe synthesis of a new morphine partial structure, 15,16-secomorphinan, is described. One of the series, (±)-15, 16-secocyclorphan (5), has the analgesic potency of morphine and exhibits good binding to the opiate receptor.
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    Diastereoselektive synthese neuartiger Mannich-BasenAusführliche Übersichten über die klassische Mannich-Reaktion: [1-4]. mittels titanderivatenÜbersichtsartikel über die Verwendung von Organotitanverbindungen in der organischen Synthese: [5-8]., vorläufige mitteilung (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1593-1597 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Diastereoselective Synthesis of Novel Mannich (Bases1) through Titanium ReagentsTrichlorotitanium dialkylamino-alkoxides (2; titanates of N, O-hemiacetals) are generated either from the corresponding lithium alkoxides and titanium tetrachloride (Scheme 1) or by addition of trichloro-dialkuylamino-titanium to aldehydes. The electrophilic (dialkylamino) alkylating reagents 2 are used to convert lithium enolates to β-dialkylamino-ketones and -esters 5 (Mannich bases), see Scheme 2 and Table. One diastereoisomer of the products 5g-5p thus obtained with cyclohexenolate is formed preferentially (66-84%). The configuration of the products of this first diastereoselective version of the Mannich reaction could not yet be determined. A typical procedure for carrying out the reaction is given.
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    Optical resolution of 7-oxabicyclo[2.2.1]hept-21-ene derivatives. Diastereoselectivity in the formation of cyanohydrine-brucine complexes (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1612-1615 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new, practical method for the optical resolution of bicyclic ketones if illusttrated by the preparation of (+)-(1R,4R)-7-oxabicyclo[2.2.1]bept-5-en-2-one ((+)-1) and (+)-(1R, 2S,4R)-2-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yul acetate ((+)-4). It involves the diastereoselective formation of a brucine complex with the corresponding cyanhydrine mixture.
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    URL: http://dx.doi.org/10.1002/hlca.19840670629
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    Transition metal complexes with bidentate ligands spanning trans-positions part XVPart XIV: See [1]. X-ray structural and 31P-NMR solution studies of some three-coordinate silver complexes of 2,11-bis[di(tert-butyl)phosphinomethyl]benzo[c]phenathrene and related ligands (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1603-1611 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of three-coordinate bis(dialkylphosphinomethyl)benzo[c]phenanthrene Ag(I) complexes, alkyl= t-Bu, (1b), and cyclohexyl, (1c), anion = BF4, CIO4, CIO4, NO3, Cl, Br, I, have been prepared and thier 31P-NMR characteristics recorded. The solid state structures of [Ag(1b)Br], [Ag(1b)Cl] and [Ag(1b)CIO4] have been determined by X-ray diffraction. The Ag atom in these complexes shows distorted trigonal geometry. Selected bond lengths and angles are as follows: Ag-P = 2.463(4) Å and 2.433(5) Å, P-Ag-P=141.6(2)° in the bromo complex, Ag-P = 2.457(2) Å and 2.427(2) Å, P-Ag-P = 142.6(1)° ion the chloro complex, and Ag-P = 2.394(2) and 2.393 (2) Å, P-AG-P = 161.5(1)° in the perchlorato complex.
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    Further Syntheses of Optically Active Verrucarinic Acid, 43rd Communication of Verrucarins and Roridins42nd Commun. : [1]. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1625-1629 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two new syntheses of verrucarinic acid (2S, 3R-dihydroxy-3-methylpentanoic acid) and its derivatives, suitably protected for the further conversion to macrocyclic trichothecenes, are described. The first one makes use of a diastereoselective alkylation of a (-)-(S)-malic acid ester and the regioselective reductin of one carboxyl function toa methyl group. The second approach involves a stereoselective addition of an allylsilane to a chiral glyoxylate.
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  • 80
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    Steuerung der katalytischen Pyridinsynthese aus Alkien and Nitrilien durch (η6-Borinato)-Liganden am CobaltHerrn Prof. Dr. R. Köster, Mülheim a. d. Ruhr, mit herzlichen Wünschen zum 60. Geburtstag gewidmet (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1616-1624 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Control of the Catalytic Synthesis of Pyridine from Alkynes and Nitriles by the (η6-Borinato)-Nigands at Cobaltη6-Borinato groups as ligands at cobalt have unique effects on the chemo- and negioselectivity of the catalytic co-cyclization of alkynes and nitriles. The turnover number of the conversion of acrylonitrile and acetylene to give 2-vinylpyridine is considerably enhanced. Cyano compounds wih polar substitutents such as amino or thio groups can also be reacted. The homogeneous reaction of HCN with acetylene giving pyridine has been achieved for the first time.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19840670630
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  • 81
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    Chemo- and Stereoselective Coordination of 5,6-Dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene by d8- and d6-Metal Carbonyls. Diels-Alder reactivity of Dienes Perturbed by Remote Olefin Complexation (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1630-1637 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The endocyclic double bond C(2), C(3) in 5,6-dimethylidene-7-oxabicyclo[2.2.1]-hept-2-ene (1) can he coordinated selectively on its exo-face before complexation of the exocyclic s-cis-butadiene moiety. Irradiation of Ru3(CO)12 or Os3(CO)12 in the presence of 1 gave tetracarbonyl [(1R,2R, 3S,4S)-2,3-η-(5,6-dimethylidene-7-oxabicyclo[2.2.1]-hept-2-ene)]ruthenium (6) or -osmium (8). Similarly, irradiation of Cr(CO)6 or W(CO)6 in the presence of 1 gave pentacarbonyl[(1R, 2R, 3S,4S)-2,3-η-(5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene)]chromium (10) or -tungsten (11). Irradiation of complexes 6 and 11 in the presence of 1 led to further CO substitution giving bed-tricarbonyl-ae-bis[(1R,2R,3S,4S)-2,3-η-(5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene)]ruthenium (7) and trans-tetracarbonyl[(1R,2R,3S,4S)-2,3-η-(5,6-dimethylidene-7-oxabicyclo-[2.2.1]hept-2-ene)]tungsten (12), respectively. The diosmacyclobutane derivative cis-m̈-[(1R,3R,3S,4S)-(5,6-dimethylidene-7-oxabicyclo[2.2.1]hepta-2,3-diyl)]bis(tetracarbonyl-osmium) (Os-Os) (9) wa also obtained. The Diels-Alder reactivity of the exocyclic s-cis-butadiene moiety in complexs 7 and 8 was found to be significantly higher than that of the free triene 1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670632
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  • 82
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    Monoolefin and Diene Cycloaddition Induced by Transition-Metal Carbonyls. Cyclodimerization of 5,6-Dimethylidene-7-oxabicyclo[2.21]hept-2-ene Catalyzed by Dodecacarbonyltriosmium (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1638-1646 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The products generated by heating 5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene (1) with Fe2(CO)9, Ru3(CO)12, Os3(CO)12, Cr(CO)3(MeCN)3, (or W(CO)5(MeCN) or by treatment with Fe-atoms have been characterized by spectroscopic methods. Apart from the expected η2- and η4-complexes of the triene 1, condensation products are formed which arise from the formal [4 + 2]-cyclodimerization of 1 involving the endocyclic double bond of one molecule and the diene moiety of a second. The [4 + 2]-cyclodimerization is catalyzed by Os3(CO)12 in MeOH and gives 1,4-epoxy-7-methoxy-2,3-dimethylidene-1,2,3,4,4a,9,9a,10-octahydroanthracene (15)). Fe-Atoms induce a stereoselective [2 + 2]-cyclodimerization pf 1 which involves its endocyclic double bond and produces the dimer 8.
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    URL: http://dx.doi.org/10.1002/hlca.19840670633
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  • 83
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    Synthese von 2,3-unsubstituierten, N-acylierten Indolen durch sigmatrope[3,3]-Umlagerung von O-Vinyl-N-phenylhydroxylaminderivaten (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1647-1649 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of 2,3-Unsubstituted N-Acylindoles by [3,3]-Rearrangement of the N-Phenyl-O-vinylhydroxylamine DerivativesSummary, Treatment of N-phenylhydroxamic acids with vinylacetate in the presence of Li2PdCl4 affords 2,3-unsubstituted N-acylindoles via hetero-Cope-rearrangement of the intermediate N-O-vinylhydroxylamine derivatives.
    Additional Material: 1 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19840670634
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  • 84
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    Mitteilugen - Communications (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1669-1669 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670637
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  • 85
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    Masthead (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984) 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670701
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  • 86
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    Photoreaction of (RS,SR)-3-Phenyl-6-hepten-2-ol. Benzene-Olefin Cycloadditions as a Synthetic Route to [5.5.5.5] Fenestranes. Part IIIFor part II of the series ‘Planarization of Tetracoordinate Carbon Atom’, see [1b]. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1930-1941 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Irradiation of (RS,SR)-3-Phenyl-6-hepten-2-ol (3n) gave the photoproducts 6n-10n. Some reactions of 6n and 8n are reported. The regio- and diastereoselectivity observed in the photoreaction of substituted 5-phenylpentenes is discussed with respect to conformational preferences of the compounds to be irradiated.
    Additional Material: 1 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19840670731
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  • 87
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    Benz[cd]indoles. Part III. A New Stereospecific Synthesis of Dihydrolysergic Acid and an Entry to 14-Substituted DerivativesPart of this work has been presented at the ‘Herbstversammlung der Schweizerischen Chemischen Gesellschaft’ at Berne, on October 18, 1982. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1942-1951 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new convenient synthesis of dihydrolysergic acid is described, which allows the preparation of substituted derivatives, especially those with different substitutents in the aromatic ring. Starting from appropriately substituted 5-nitro-2-tetralones, the synthesis leads via a tricyclic isonitrile to the indole-ring closure as the last step, thus circumventing the troublesome protection/deprotection of the latter.
    Additional Material: 1 Tab.
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  • 88
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    Triaziridines. Part IIIPart II, see [1].. Triaziridine, azimine, and triazene: A SCF study of the energy and structure of N3H3-isomers (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1918-1929 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The portions of the N3H3 singlet potential energy surface corresponding to triaziridines (1), azimines (2) and triazenes (3) have been calculated by ab initio SCF using 3-21G, 6-31G, and 6-31G** basis sets. Minima and transition states were located by force gradient geometry optimization. The most important computation results are: (1) Triaziridines (1): The configuration at the 3 N-atoms is pyramidal. There are 2 stereoisomers, 1a and 1b. The c,t-isomer 1a has less energy than the c,c-isomer 1b. The 2 stereoisomerizations by N-inversion hve rather high activation energies. The N,N bonds in 1 are longer and weaker (STO-3G estimation) than in hydrazine. The N-homocycle 1 exhibits less ring strain than the C-homocycle cyclopropane or three-membered heterocycles. (2) Azimine (2): All 6 Atoms are in the same plane. There are 3 stereoisomers, 2a, 2b, and 2c. The order of ground state energies is (Z,Z) 〈 (E,Z) ≫ (E,E). The 2 N,N bond lengths correspond to multiplicity 1½. The electronic structure of 2 corresponds to a 1,3-dipole with almost equal delocalization of the 4 π-electrons over all 3 N-atoms. The negative net charge at the central N-atom is much less than that at the terminal N-atoms. Azimines should behave as π-donors in complexation with transition metals (3) Triazene (3): All 6 atoms are in the same plane. There are 2 stereoisomers, 3a and 3b. The order of ground-state energies is (E) 〈 (Z). The stereoisomerization proceeds as pure N-inversion. N-Inversion has a high energy barrier inversion at N(1) is faster than at N(2). One of the N,N bond lengths is typical for a double, the other for a single bond. The electronic structure of triazene 3 entails rather localized π- and p-electron pairs at N(1),N(2) and at N(3). Triazenes should behave as p-donors in complexation with transition metals. (4) -N3H3-Isomers: The order of ground-state energies is 3 〈 2 〈 1. The energy differences between these constitutional isomers are much larger than between the stereoisomers of each. The [1,2]-H shifts for conversions of 2 to 3 and the [1,3]-H shift for tautomerization of 3 have relatively high activation energies; both shifts can be excluded as modes of thermal, unimolecular transformations.
    Additional Material: 2 Ill.
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  • 89
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    The Reaction of 4-Hydroperoxy-2,4,6-trimethylcyclohexa-2,5-dienone with Acetaldehyde. Formatino of the Bis(peroxyacetal) (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1952-1956 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of 4-hydroperoxy-2,4,6-trimethylcyclohexa-2,5-dienone with acetaldehyde using trimethylsilyl trifluoromethanesulfonate as catalyst gives 1,1′-bis[(1,3,5-trimethyl-4-oxo-2,5-cyclohexadienyl) peroxy]diethyl ether (7) in 70% yield. The structure of this unusual acetal was determined by X-ray analysis.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19840670733
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  • 90
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    The chemistry of drugs part IVPart III, see [1]., Configurations of antimalarials derived from qinghaosu: Dihydroqingyhaosu, artemether, and artesunic acid (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1515-1522 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The structures of the antimalarials dihydroqinghaosu (2), artemether (3), and artesunic acid (7a) derived from qinghaosu were elaborated by 1H-NMR spectroscopy, and supported with X-ray data obtained for 2 and 3. Several new derivatives, useful for the chemical characterization of dihydroqinghaosu (2) and artesunic acid (7a), were prepared.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19840670615
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  • 91
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    Deoxy-nitrosugars, 7th communication6th Communication: [1]. Synthesis of methyl shikimate and of diethyl phosphashikimate from D-ribose (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1562-1567 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The chain elongation of the deoxy-nitroribose 6 by a Michael addition to the vinyl-phosphonate 7 followed by a solvolysis gave the heptulosephosphonate 11 (87%). From 11, the key intermediates 15 and 16 (77%) were obtained by a highly diastereoselective reduction, followed by detritylation, periodate cleavage, and silylation. Methoxycarbonylation of 15 and 16 gave 17 and 18 which were converted into methyl shikimate (21; 79%) by intramolecular olefination and partial deprotection. Similarly, phosphonoylation of 16 gave 22 (99%) which was transformed into the diethyl phosphashikimate 2 (53% from 6).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670621
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  • 92
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    Mitteilungen - Communications (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 2029-2030 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670743
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  • 93
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    Errata (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 2028-2028 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670742
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  • 94
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    Masthead (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984) 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670801
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  • 95
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    On the Nature of the 7-Norbornadienyllithiums. Preliminary Communication (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 2029-2036 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Lithium reductions of 7-chloronorbornadiene and of bis(7-norbornadienyl)mercury both provide (C7H7)2Li2 (5a). This product is accompanied by C7H7Li2Cl (5c) in the first case, and by C7H7Li (5b) in the second. The theoretically anticipated properties of all three organolithiums are apparent in the consistent Cs symmetry of their hydrocarbon ligands, their protolytic destruction by 12-crown-4, and their significant J(C(7), Li) (5a, 7.6; 5b, 16.0; 5c 8.9 Hz).
    Additional Material: 3 Ill.
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  • 96
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    Novel Variant of the Tricyclooctanone Approach to Cyclopentanoid Natural Products. Synthesis of (±)-Coriolin. Preliminary Communication (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 2023-2027 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A total synthesis of the antitumor sesquiterpene coriolin (9; racemic) in 11 steps from 3,3,6-trimethylbicyclo[2.2.2]oct-7-ene-2,5-dione (2a/2b) is described (yield 2a/2b→8: 28%). The sequence is unprecedentedly short and avoids difficult separation problems. The key step in the scheme is a novel facet of oxadi-π-methane photochemistry, i.e., the steering by subtle steric effects of the β,γ-unsaturated ∊-diketone to undergo a regioselective photorearrangement involving one β,γ-enone partial chromophore. Furthermore, the overall phototransformation, which can be carried out at unusually high concentrations (≥20% solutions), involves also a Norrish type I process equilibrating the two epimeric starting enediones 2a and 2b in favour of the desired stereoisomer.
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  • 97
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    Synthese von optisch aktiven Carotinoiden mit 3,5,6-Trihydroxy-5-6-dihydro-β-Endgruppen (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 2043-2056 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Syntheses of Optically Active Carotenoids with 3,5,6-Trihydroxy-5,6-dihydro β-End GroupsFor the specification of the relative and absolute configuration in carotenoids with 3,5,6-trihydroxy-5-6-dihydro β-end groups, several ionone derivatives and carotenoids bearing this end group were synthesized. Acid-catalyzed hydrolysis of (3S,5S,6R)- acetoxy-5,6-epoxy-5,6-dihydro-β-ionone (7) and of its (3S,5R,6S)-isomer (13) gave the diols 8 and 15, respectively, with exclusive inversion at c(5) (Scheme 2). Compared to this, mild acid hydrolysis of caroten-5-6-expoxides in the presence of H2O resulted in the formation of 5,6-diols with either inversion or retention of the configuration at C(6) (Scheme 3). Spectroscopic data allowed us to distinguish the relative configurations (3R*,5S*,6S*) (see A), (3R*,5R*,6R*) (see B), (3R*,5S*,6R*) (see C), and (3R*,5R*,6S*) (see D), of the 3,5,6-trihydroxy-5-6-dihydro β-end groups. Syntheses of the optically active carotene-hexols 20 and 21 and comparison with published data led to a revision of the structure of mectrazanthin (now formulated as 20), heteroxanthin (now formulated as 28), and further carotenoids with 3,5,6-trihydroxy end groups.
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    URL: http://dx.doi.org/10.1002/hlca.19840670804
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  • 98
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    The Photoisomerization of 1,2,3,4,5-Pentamethyl-5-vinyl-1,3-cyclopentadiene (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 2057-2062 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The title compound 1 is shown to give, both upon direct irradiation at 254 nm and upon acetophenone-sensitized photolysis at 300 nm, the syn-vinyl-pentamethylhousene 5, which spontaneously rearranges in a [3,3]0sigmatropic process to give the bicyclo[3.2.0]heptadiene skeleton 2. Based on the photochemical behaviour of selectively deuterated starting material, the suggestion is made that the direct photolysis produces the vinylhousene skeleton by a classic electrocyclization, whereas the sensitized reaction reaches the same target via a di-π-methane rearrangement. The bicyclo[3.2.0]heptadiene derivative 2 give pentamethylhomoprismane 3 upon prolonged irradiation at 254 nm.
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    URL: http://dx.doi.org/10.1002/hlca.19840670805
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  • 99
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    Conversion of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (mptp) and its 5-methyl analog into pyridinium saltsDedicated to Prof. Dr. H.C. Beyerman of the Laboratory of Organic Chemistry at the Technical Highschool in Delft, the Netherlands, on the occasion of his 65th birthday. (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 2037-2042 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Monoamine oxidase B metabolizes 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP; 1) first to 1-methyl-4-phenyl-2,3-dihydropyridinium salt (MPDP+; 5), and then to 1-methyl-4-phenylphridinium salt (MPP+; 7). Chemical synthesis of MPDP+ and its 5-methyl analog 6 was accomplished from the N-oxides 3 and 4 of MPTP and its 5-methyl analog, respectively, by a Polonovski reaction. Oxidation of MPDP+ to MPPM+ was accomplished with air, and greatly accelerated by Pt catalyst. Reduction of MPDP+ and MPP+ with NaBH4 afforded MPTP.
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    URL: http://dx.doi.org/10.1002/hlca.19840670803
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  • 100
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    Photochemical reactions. 140th Communication139th Communication, see [1]. Acid-catalyzed rearrangement and electron transfer photooxygenation of cyclopropanols and their silyl ethers (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1748-1754 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On acid-catalyzed hydrolysis, the tricyclic compounds 2 and 10, incorporating cyclopropyl-silyl-ether moieties undergo rearrangement to the cis-decalones 3 and 7, respectively. Hydrolysis of 2 and 10 in the presence of oxygen leads additionally to the formation of the 1,2-dioxolan-3-ols 9 and 13, respectively, which involves an electron-transfer oxygenation process as could be demonstrated by photooxygenation of the silyl ether 10 and the cyclopropanol 14 in the presence of 9,10-dicyanoanthracene. The configurations of 3 and 9 were assigned by X-ray analysis of the latter compound as well as of the p-nitrobenzoate 8 of 3.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670712
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