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  • 1990-1994  (9)
  • 1960-1964
  • Organic Chemistry  (4)
  • Physical Chemistry  (3)
  • Rhenium  (3)
  • 1
    Electronic Resource
    Electronic Resource
    The quadruply bondedbis-carboxylatescis-Re2(μ-O2CCH3)2X4L2 (X = halide;L = neutral donor) as synthons in dirhenium chemistry (1994)
    Springer
    Journal of cluster science 5 (1994), S. 173-184 
    Details
    ISSN: 1572-8862
    Keywords: Rhenium ; dimetal comptexes ; phosphine ligands ; carboxylatebridged complexes ; redox chemistry ; preparation ; structure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: Abstract The reactions of the quadruply bonded dirhenium(III) carboxylatescis-Re2(μ-O2CR)2X4L2 (X=CI or Br; L=a monodentate donor) with monodentate, bidentate, and tridentate phosphine donors result in several types of redox behavior, usually involving partial or complete reductive decarboxylation of the dirhenium unit. Examples of dirhenium(VI, II), dirhenium(IV, II), dirhenium(III, II), and dirhenium(II, II) complexes, in which Re-Re bond orders of 4, 3.5, 3, l, or zero are encountered, have been isolated and repre-sentative examples structurally characterized. The course of these reactions is dependent upon the nature of the phosphine. The scope of this remarkably rich chemistry is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01165498
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  • 2
    Electronic Resource
    Electronic Resource
    The oxidative addition of hydrogen sulfide to the electron-rich triple bond: The isolation and characterization of compounds that contain the Re2(μ-H)(μ-SH) cluster unit (1991)
    Springer
    Journal of cluster science 2 (1991), S. 259-270 
    Details
    ISSN: 1572-8862
    Keywords: Rhenium ; clusters ; hydrido-bridged ; hydrosulfido-bridged ; preparation ; structure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: Abstract The reactions of Re2X4(μ-dppm)2 (X=Cl or Br; dppm=Ph2PCH2PPh2) with H2S in THF afford the dirhenium (III) complexes Re2(μ-H)(μ-SH)X4(μ-dppm)2, the first examples of the oxidative addition of an S-H unit across an electron-rich metal-metal triple bond. The bromide complex Re2(μ-H)(μ-SH)Br4(μ-dppm)2 (C2H5)2O crystallizes in the space group P21/n witha=16.631(2) Å,b=15.967(3) Å,c=19.904(2) Å, β=92.698(7)°,V=5279(2) Å3, andZ=4. The structure which was refined toR=0.053 (R w=0.070) for 4903 data withI〉3.0σ(I), shows the presence of an edge-shared bioctahedral geometry with a very short Re-Re distance of 2.4566(7) Å. While the hydrogen atoms of the μ-H and μ-SH ligands were not located in the X-ray structure determination, their presence is confirmed by IR and1H NMR spectroscopy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00702956
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  • 3
    Electronic Resource
    Electronic Resource
    The oxidative addition of diphenylphosphine and monophenylphosphine to the electron-rich rhenium-rhenium triple bond. The isolation and characterization of compounds that contain the four-center Re(μ-X)(μ-PR2)Re cluster (X=halide) (1992)
    Springer
    Journal of cluster science 3 (1992), S. 83-102 
    Details
    ISSN: 1572-8862
    Keywords: Rhenium ; dimetal clusters ; hydrido-complexes ; phosphidobridged ; preparation ; structure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: Abstract Diphenylphosphine oxidatively adds to the Re≡Re bonds of Re2 X 4(μ-dppm)2 (X=Cl or Br; dppm=Ph2PCH2PPh2) and Re2Cl4(μ-dpam)2 (dpam=Ph2AsCH2AsPh2) to afford the dirhenium(III) complexes Re2(μ-X)(μ-PPh2)HX 3(μ-LL)2. The dppm complexes have also been prepared from the reactions of Re2(μ-O2CCH3)X 4(μ-dppm)2 with Ph2PH, and a similar strategy has been used to prepare Re2(μ-Cl)(μ-PPh2)HCl3(μ-dmpm)2 (dmpm=Me2PCH2PMe2) from Re2(μ-O2CCH3)Cl4(dmpm)2. Phenylphosphine likewise reacts with Re2 X 4(μ-dppm)2 to give Re2(μ-X)(μ-PHPh)HX 3(μ-dppm)2. An X-ray crystal structure determination on Re2(μ-Cl)(μ-PPh2)HCl3(μ-dppm)2 confirms its edge-shared bioctahedral structure. This complex crystallizes in the space group $$R\bar 3$$ (No. 148) witha=21.699(3) Å, α=84.50(4)°,V=10084(5) Å3, andZ=6. The structure was refined toR=0.049 (R w 0.069) for 5770 data withI〉3.0σ(I). The Re-Re distance is 2.5918(7) Å. Oxidation of the bromide complex Re2(μ-Br)(μ-PPh2)HBr3(μ-dppm)2 with NOPF6 produces the unusual dirhenium(III, II) cation [Re2(μ-H)(μ-Br)[P(O)Ph2]Br2(NO)(μ-dppm)2]+ which has been structurally characterized as its perrhenate salt, [Re2(μ-H)(μ-Br)[P(O)Ph2]Br2(NO)(μ-dppm)2]ReO4 · 2CH2Cl2. This complex crystallizes in the space group $$P\bar 1$$ (No. 2) witha=14.187(7) Å,b=16.419(5) Å,c=16.729(5) Å, α=98.76(2)°, β=110.11(3)°, γ=104.66(3)°,V=3414(6) Å3,Z=2. The structure was refined toR=0.040 (R w =0.051) for 5736 data withI〉3.0σ(I). The presence of a phosphorus-bound [P(O)Ph2]− ligand, a linear nitrosyl and a bridging hydrido ligand has been confirmed. The Re-Re distance is 2.6273(8) Å.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00814613
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  • 4
    Electronic Resource
    Electronic Resource
    Design and Synthesis of Novel Opiate Antagonists with LH-Stimulating Properties (1990)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 73 (1990), S. 326-336 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Opiate antagonists stimulate the release of LH and might, therefore, contribute to an innovative therapy for the treatment of numerous clinical syndromes characterized by hypofunction of the HHG axis. The purpose of this work was to design and synthesize pure opiate antagonists useful for this therapy. Me, Et, Pr, and PhCH2 groups were introduced at the crucial 14β-position of morphines and morphinans via a hetero-Diels-Alder key step starting from thebaine derivative 1 and tested for opiate antagonism and LH-stimulating activity. Me-, Et-, and Pr-substituted compounds 11a-c were stronger antagonists than naltrexone, whereas Pr and PhCH2 substituents in 11c, 11d, 9d, 9d3, 9d4, and 9d5 led to orally active LH stimulators. Based on our finding that the μ-antagonists 12 and 11b5 showed no LH stimulation, we conclude that a combination of both μ-and χ-antagonism is necessary for potent LH stimulation.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19900730212
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  • 5
    Electronic Resource
    Electronic Resource
    Ambident reactivity of aryloxide ions towards 1,3,5-trinitrobenzene, low-temperature characterization of the elusive Oxygen-bonded σ-complexes by 1H and 13C NMR spectroscopy (1993)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 6 (1993), S. 71-82 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The ambident reactivity of phenoxide ion towards 1,3,5-trinitrobenzene (TNB) was re-examined by means of a novel reaction system(CD3CN-glyme-d10) which allows the investigation of species formed at low temperatures (-40°C), contrasting with previous studies in dimethyl sulfoxide (DMSO) at ambient temperature. The new method coupled with 400 MHz NMR spectroscopy has allowed the definitive observation of both O- and C-bonded phenoxide σ-complex adducts for the first time, confirming the formation of the former through kinetic control and of the latter through thermodynamic control. The corresponding O-bonded σ-adduct in the TNB-mesitoxide system (whereC-bonded σ-adduct formation is not possible but where there is competing nitro group displacement) has also been characterized by 1H and 13C NBR. Another O-bonded aryloxide adduct characterized is that from the reaction of TNB with3,5-di-tert-butylphenoxide; in this system there is also competing NO2 displacement. Stereoelectronic factors in the O-bonded σ-adducts and aryl ethers are discussed.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610060202
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  • 6
    Electronic Resource
    Electronic Resource
    Lipidic peptides, I. Synthesis, resolution and structural elucidation of lipidic amino acids and their homo- and hetero-oligomers (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 1175-1183 
    Details
    ISSN: 0170-2041
    Keywords: Amino acids, fatty ; Peptides, lipidic ; Drug delivery ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The α-amino acids with long alkyl side chains, the so-called lipidic amino acids 1a-e, and their homo-oligomers, the lipidic peptides 1p-aj, represent a class of compounds which combine the structural properties of peptides and proteins with the characteristics of lipids and membranes. The amino acids were synthesised from the appropriate alkyl bromide and diethyl acetamidomalonate. Resolution was made chemically, by forming diastereomers of the amino acid esters with an optically pure α-pinene derivative. The protected homooligomers were synthesised in solution with the assistance of a water-soluble carbodiimide coupling agent. In order to modify the physical and chemical properties of the peptides, a series of protected hetero-oligomers were prepared, by similar methods, incorporating either other amino acids (3a - d, 7a - i) or side-chain-substituted lipidic amino acids (6a-d).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001215
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis and Oral Uptake Studies of Lipidic and Glyco-Lipidic Conjugates of β-Lactam Antibiotics (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 685-688 
    Details
    ISSN: 0170-2041
    Keywords: Amino acids, lipidic ; Antibiotics ; Drug delivery ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Lipidic and glyco-lipidic cephalosporin conjugates 1c and 1i were synthesised as diastereomeric mixtures to improve their oral absorption. 2-(tert-Butoxycarbonylamino)tetradecanoic acid was condensed with thiazole 1d and by following basecatalysed hydrolysis of the fully protected rac-1e, the free acid rac-1f was produced. This was then used to acylate the carboxy-protected cephalosporin analog 1g by using a modified Vilsmeier reaction. Removal of the protecting groups of 1b resulted in conjugate 1c. Cephalosporin conjugate li, which contains a sugar moiety in addition to a lipidic amino acid residue, was synthesised to produce a drug conjugate with both lipophilic and hydrophilic properties [radiolabelled (14C) analogs 1a, 1c and 1i were also synthesised]. The radio-labelled parent 1a and conjugates 1c and 1i were administered orally to rats and uptake of the radiolabel in the blood, various organs, urine and faeces was determined. The results showed that an increase in lipophilicity caused an increase in the oral uptake, suggesting that conjugation to lipidic amino acids and peptides is a useful approach to the improvement of the absorption of poorly absorbed drugs.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940709
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  • 8
    Electronic Resource
    Electronic Resource
    Kinetics of solvolysis of 1-acetyl-4-(1-ethoxycarbonyl-1-cyano) methylene-1,4-dihydroquinoline in undried DMSO-d6· formation of Acetic Anhydride as an intermediate (1992)
    New York, NY : Wiley-Blackwell
    International Journal of Chemical Kinetics 24 (1992), S. 447-454 
    Details
    ISSN: 0538-8066
    Keywords: Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The kinetics of solvolysis of the title compound (QAc) in undried DMSO-d6 to give 4-(1-ethoxycarbonyl-1-cyano)methylquinoline (QH) and HOAc at ambient temperature were investigated by 1H nmr spectrometry. With a limited excess of water the solvolysis follows a three-step process of \documentclass{article}\pagestyle{empty}\begin{document}$ {\rm QAc} + {\rm H}_2 {\rm O}\mathop \to \limits^{k_1} {\rm QH} + {\rm HOAc}, $\end{document} , and \documentclass{article}\pagestyle{empty}\begin{document}$ {\rm Ac}_{\rm 2} {\rm O} + {\rm H}_2 {\rm O}\mathop \to \limits^{k_3} {\rm 2\,HOAc}, $\end{document} where k2 〉 k1 and k3 〈 k1. Addition of pyridine-d5 to the reaction mixture markedly catalyzes the overall solvolysis, while addition of CF3CO2D to the reaction mixture simplifies the kinetics to pseudo first-order in [QAc] with k = 4.3 × 10-3 min-1.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/kin.550240505
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  • 9
    Electronic Resource
    Electronic Resource
    Kinetics of a second order reaction involving two intermediate second order reactions (1992)
    New York, NY : Wiley-Blackwell
    International Journal of Chemical Kinetics 24 (1992), S. 455-466 
    Details
    ISSN: 0538-8066
    Keywords: Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: We have studied the kinetics of a reaction in which starting materials A and B react to form the products C and D directly, as well as by way of two additional intermediate reactions. In the first intermediate reaction, A and C react to form D and E, and in the second intermediate reaction, B and E react to form 2C. There are three conservation laws, which effectively reduce the number of variables to two, resulting in nonlinear coupled first order differential equations for [A](t) and [B](t). These equations are readily solved by standard numerical procedures, for various values of the relative reaction rates and starting concentrations. Our results are used to fit experimental data for the case in which A and B are 1-acetyl-4-(1-ethoxycarbonyl-1-cyano)methylene-1,4-dihydroquinoline and water, for which the first and third reverse reactions can be neglected.
    Additional Material: 12 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/kin.550240506
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