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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis and Structures of Bis(tetramethylipiperidino)aluminum Halides-X-ray Crystal Structures of tmp2AlX (X = Cl, Br, I) and [tmp2A1(μ-F)l2 (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 1047-1052 
    Details
    ISSN: 0009-2940
    Keywords: Bis(tetramethylipiperidino)aluminum halides ; Alkoxy((tetramethylpiperidino)aluminum halides ; 27Al-NMR spectra ; Aluminum ; Amides ; Synthetic methods ; Bridging ligands ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: N-Lithio-2,2,6,6-tetramethylpiperidine [Li(tmp)] reacts with AlX3 (X = Cl, Br) in diethyl ether/ n-hexane solution to generate the products of substitution and ether cleavage, [tmpAl(X)(μ-OEt)], (la, X = Cl; 1b, X = Br). However, when the reaction is allowed to proceed in n-hexane alone, an almost quantitative yield of compounds tmp2AlX (2a, X = Cl; 2b, X = Br; 2c, X = I) is obtained. According to 27AI-NMR spectroscopy, mass spectroscopy, cryoscopy, and X-ray crystal structure determinations, these compounds are monomeric in the solid state, in solution, and in the gas phase. 2b reacts with AgBF4 yielding the fluoride-bridged dimer (tmp2AlF), 2d, as shown by X-ray crystal structure determination.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971300805
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of 21-(3-Methylbutyl)cholest-5-ene-3β,3′,25-triol and 21-(2-Methylpropoxy)cholest-5-ene-2′,3β,25-triol, the First “Double Side Chain” Cholesterol Analogues (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1997-2001 
    Details
    ISSN: 0947-3440
    Keywords: Cholesterol ; Steroid side chain construction ; Alkylations ; Synthetic methods ; Steroids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 21-(3-hydroxy-3-methylbutyl)- and 21-(2-hydroxy-2-methylpropoxy)cholestane derivatives 3 and 5, formally double chain hybrid (20R)- and (20S)-cholesterol analogues, were synthesized. The C-22 to C-27 section of the 25-hydroxycholestane side chain was established by stereoselective alkylation with 5-bromo-2-methyl-2-(triethylsilyl)oxypentane of the pregnanoic ester 8, derived from 3β-acetoxyandrost-5-en-17-one (7). Reduction of the ester 9 to the 21-alcohol 10 permitted elaboration of a second hydroxylated side chain, either via the tosylate 11 by alkynation/hydrogenation (yielding intermediate 13) or by alkylation of 10 with bromoacetate (yielding 14) followed by reaction with methyl magnesium bromide.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970928
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  • 3
    Electronic Resource
    Electronic Resource
    Functionalized Ozonides by Substitution Reactions of Chlorinated Ozonides with Difunctional Alcohols (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 2581-2585 
    Details
    ISSN: 0947-3440
    Keywords: Ozonides, functionalized ; Substitutions ; Alcohols ; Aldehydes ; Synthetic methods ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Substitution of 3-chloro-3,5-bis(chloromethyl)-5-methyl-1,2,4-trioxolane (3) with allyl alcohol gave the corresponding diastereomeric allyloxy-substituted ozonides 4, which were converted into diozonides 7 by ozone treatment. Substitutions of 3 with ethanediol or with 1,3-propanediol gave the corresponding hydroxyalkoxy-substituted ozonides 8, 14, which were oxidized to the corresponding aldehydes 10, 16. Reaction of 3,5-dichloro-3,5-bis(chloromethyl)-1,2,4-trioxolane (1a) with ethanediol gave the corresponding bis(hydroxy)-substituted ozonide 19 as well as a bicyclic ozonide 18 by reaction of 1a with ethanediol in a ratio of 1:1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719971225
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  • 4
    Electronic Resource
    Electronic Resource
    Recent Advances in Organic Synthesis under High Pressure (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 623-635 
    Details
    ISSN: 0947-3440
    Keywords: High-pressure chemistry ; Nucleophilic aromatic substitution ; Cycloadditions ; Synthetic methods ; Synthesis under neutral, mild conditions ; Supramolecular chemistry ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The most recent successes achieved in organic synthesis by use of high-pressure technique are reviewed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970404
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis of an Epoxide- and Carbonate-Containing 6-/10-Membered Bicyclodienediyne Analogue of the Neocarzinostaitin Chromophore (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 961-965 
    Details
    ISSN: 0947-3440
    Keywords: C—C coupling ; Dienediynes ; McMurry reaction ; Neocarzinostatin ; Synthetic methods ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The monocyclo-diendiyne → bicyclo-trienediyne strategy for obtaining dienediyne models of the antitumor antibiotic neocarzinostatin chromophore (1) was extended from generating 6-/11-membered bicyclotrienediynes (e.g. 2 → 4) to generating the 6-/10-membered bicyclotrienediyne 5. In the preparatory steps (Scheme 2), the bistriflate 10 was successively coupled with alkynes 9 and 11. Via the dienediynediol and its subsequent oxidation with the Dess-Martin periodinane, we obtained the monocyclic dienediyne keto aldehyde 13. Cyclization of 13 with low-valent titanium afforded the bicyclotrienediyne 5 in 42% yield (Scheme 3). Compound 5 was converted in five steps - namely ketal cleavage, monosilylation of the resulting diol 14, asymmetric Sharpless epoxidation, desilylation and carbonate formation - into the dienediyne epoxycarbonate 3. The structure of the latter is more closely related to the neocarzinostatin chromophore than our earlier analogues.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970527
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  • 6
    Electronic Resource
    Electronic Resource
    Strategy for the Synthesis of Epoxide- and Carbonate-Containing Dienediyne Models of the Neocarzinostatin Chromophore - Application to the 6-Ring/11-Ring Case[1] (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 947-959 
    Details
    ISSN: 0947-3440
    Keywords: C-C coupling ; Dienediynes ; Enol triflates ; McMurry reaction ; Neocarzinostatin ; Synthetic methods ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A novel synthetic strategy leading to bicyclic dienediyne models of the chromophore 1 of the anti-tumor antibiotic neocarzinostatin is described. Its key step is a ring-closing McMurry reaction of the dienediyne keto aldehydes 17 or 23. It leads to dienediynediols (compounds 19 and 24, respectively) or to trienediynes (compounds 18 and 25, respectively). Low temperatures favor the formation of dienediynediols while high temperatures favor the formation of trienediynes, so that the McMurry reactions of keto aldehyde 23 show an almost perfect temperature-dependent chemoselectivity (Scheme 6). The trienediyne 25 contains a ketal group which was removed by acid-catalyzed methanolysis (Scheme 8). The resulting diol 31 was mono-tert-butylsilylated to provide the allyl alcohol 36 (Scheme 10). It was epoxidized regio- and stereoselectively with Sharpless' asymmetric epoxidation reagent. The resulting epoxide 37 was converted into the dienediyne epoxycarbonate syn-33 in the final step of a sequence totaling seven steps and 5% yield starting from the bistriflate 3b; 3b itself is accessible from 2-formylcyclohexa none in two steps and 47% overall yield. The dienediyne epoxycarbonate syn-33 is the first synthetic congener of the neocarzinostatin chromophore furnished both with the - correctly configured - epoxide and carbonate rings.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970526
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  • 7
    Electronic Resource
    Electronic Resource
    The Paternò-Büchi Reaction of 3-Heteroatom-Substituted Alkenes as A Stereoselective Entry to Polyfunctional Cyclic and Acyclic MoleculesDedicated to Professor G. A. Olah on the occasion of his 70th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1627-1634 
    Details
    ISSN: 0947-3440
    Keywords: Photochemistry ; Synthetic methods ; Oxetanes ; Diols ; Amino alcohols ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The preparation of 3-heteroatom-substituted oxetanes by the Paternò-Büchi reaction, and their application in synthesis are reviewed. 3-Oxetanols and 3-aminooxetanes are the two most important oxetanes in this respect. By tuning the electronic properties of the enol and enamine substrates, a successful photocycloaddition to carbonyl compounds, with high yield, is possible. Since the oxetane formation proceeds stereoselectively, diastereomerically pure products are readily accessible, which can then be used in further transformations. To this end, regioselective ring-opening reactions have been developed, some of which will be discussed in this account.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970803
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  • 8
    Electronic Resource
    Electronic Resource
    Alkenylidenes in Organic Synthesis (1997)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 36 (1997), S. 1164-1170 
    Details
    ISSN: 0570-0833
    Keywords: carbenes ; carbenoids ; cyclizations ; rearrangements ; synthetic methods ; Carbenes ; Carbenoids ; Cyclization ; Rearrangement ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Alkenylidenes R2C=C: (= alkylidene carbenes) undergo regio- and stereoselective intramolecular C—H insertion reactions that are excellently suited for the synthesis of cyclopentenes. The 1, 2-shifts occurring with R=H and R=Ar are useful for the preparation of alkynes. Alkenylidenes are efficiently generated from carbonyl compounds by diazomethylation, from vinyl halides by α-elimination, from alkynyliodonium salts by addition of nucleophiles, and from alkynes by retro-1, 2-shifts. Specific applications of the various methods, particularly in the synthesis of natural products, are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.199711641
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  • 9
    Electronic Resource
    Electronic Resource
    Regio- and Stereoselective Syntheses with Organocopper ReagentsDedicated to Professor Klaus Hafner on the occasion of his 70th birthday (1997)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 36 (1997), S. 186-204 
    Details
    ISSN: 0570-0833
    Keywords: chirality ; catalysis ; copper ; reagents ; synthetic methods ; Homogeneous catalysis ; Chirality ; Copper ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Of all of the organometallic reagents currently used to form carbon-carbon bonds, organocopper reagents rank amongst the most important. Interest in these reagents centers not only on their regioselectivity, but also increasingly on their application in stereoselective transformations (principally Michael additions and SN2′ reactions); the use of suitable substrates or chirally modified cuprates can lead to highly diastereo- and enantioselective reactions. Simultaneously, extensions of methods for the preparation and application of these reagents (for example functionalized organocopper species and Lewis acid catalysis, respectively) have opened up new horizons for organocopper reagents. Mechanistically, the reactions are well-documented and understood, but this aspect of the subject has not kept pace with the many rapid developments in preparative chemistry. Organocopper ragents have proved to be indispensable in the synthesis of complex natural products and pharmaceuticals, chiral auxiliaries, and molecules with interesting structural features. In this review we will discuss some of the more recent important developments in this area; the organization will follow the type of selectivity (regio-, diastereo-, and enantioselectivity).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.199701861
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  • 10
    Electronic Resource
    Electronic Resource
    Homoleptic Metal Carbonyl Cations of the Electron-Rich Metals: Their Generation in Superacid Media Together with Their Spectroscopic and Structural CharacterizationEditorial note: In this review the recommendations of IUPAC Nomenclature have not been followed. The formulas of the neutral coordination compounds have not been enclosed by square brackets in order to distinguish more clearly the neutral compounds from ionic complexes and polyanions. (1997)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 36 (1997), S. 2402-2425 
    Details
    ISSN: 0570-0833
    Keywords: carbonyl complexes ; cations ; superacidic systems ; synthetic methods ; transition metals ; Carbonyl ligands ; Cations ; Superacidic systems ; Synthetic methods ; Transition metals ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Homoleptic carbonyl cations of the electron-rich metals in Groups 8 through 12 are the newest members of the large family of transition metal carbonyls. They can be distinguished from typical metal carbonyl complexes in several respects. Their synthesis entails carbonylation of metal salts in such superacids as fluorosulfuric acid and “magic acid” HSO3F—SbF5. Thermally stable salts with [Sb2F11]- as counterion are obtained with antimony pentafluoride as reaction medium. Both the [Sb2F11]- anion and superacid reaction media have previously found little application in the organometallic chemistry of d-block elements. Also unprecedented in metal carbonyl chemistry are the coordination geometries with coordination numbers 4 (square-planar coordination) and 2 (linear coordination) for the cation. Formal oxidation states of the metals, and the charges of the complex cations, extend from + 1 to +3: thus CO is largely σ-bonded to the metal, and the CO bond is strongly polarized. Minimal metal → CO π-backbonding and a positive partial charge on carbon are manifested in long M—C bonds, short C—O bonds, high frequencies for C—O stretching vibrations (up to 2300 cm-1), and small 13C NMR chemical shifts (up to δc, = 121). Prominent examples of these unusual homoleptic carbonyl cations, which were recently the subject of a Highlight in this journal, include the first carbonyl cation of a p-block metal [Hg(CO)2]2+, the first trivalent carbonyl cation [Ir(CO)6]3+, and the first multiply charged carbonyl cation of a 3d metal [Fe(CO)6]2+. In this overview we propose to (a) outline the historical origins of cationic metal carbonyls and their methods of synthesis; (b) present a summary of the general field of carbonyl cations, which has developed over a yery short period of time; (c) discuss the structural and spectroscopic characteritics of metal-CO bonding; (d) discuss the special significance associated with reaction media and the [Sb2F11]- anion; and (e) point to the most recent results and anticipated future developments.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.199724021
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  • 11
    Electronic Resource
    Electronic Resource
    Syntheses with ketones, sulfur, and ammonia or amines at room temperatureSimple syntheses and chemical behavior of new heterocyclic ring systems, part 2. Part 1: F. Asinger and M. Thiel, Angew. Chem. 70, 667 (1958). Cf. also F. Asinger, W. Schäfer, K. Halcour, A. Saus, and H. Triem, Angew. Chem. 75, 1050 (1963); Angew. Chem. internat. Edit. 3, 19 (1964). (1967)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 6 (1967), S. 907-919 
    Details
    ISSN: 0570-0833
    Keywords: Ketones ; Sulfur ; Amines ; Heterocycles ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A large number of preparatively interesting compounds have become readily available by the simultaneous action of sulfur and ammonia or amines on ketones. Direct syntheses of Δ3-thiazolines, Δ3-imidazoline-5-thiones, 5,6-dihydro-4H-1,4-thiazines, and the 1,2,3,4,5,6-hexathiocane system from ketones, sulfur, and ammonia or amines, and further possibilities for the synthesis of these heterocyclic systems have been proposed. Other heterocycles containing N or N and S (thiazoles, thiophenes, thiazolidines, tetrahydrothiazolo[2,3-c]-1,4-thiazines, thiomorpholines, 4-amino-2H-imidazoles, etc.) are readily obtainable by further reactions of these compounds. Hydrolysis of the Δ3-thiazolines yields α-mercapto ketones, which are the starting materials for other syntheses. Most of the syntheses described proceed at room temperature and at normal pressure.
    Additional Material: 10 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196709071
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  • 12
    Electronic Resource
    Electronic Resource
    New Methods of Preparative Organic Chemistry VThe papers in the preceding series have been published in four volumes by Verlag Chemie, Weinheim/Bergstr.; English edition: Academic Press New York-London. Volume V will appear shortly.: Organic Syntheses with Imides of Sulfur Dioxide (1967)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 6 (1967), S. 149-167 
    Details
    ISSN: 0570-0833
    Keywords: Imides ; Sulfur dioxide ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cycloadditions and other reactions of compounds containing the groups N=SO and N=S=N are reviewed.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196701491
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  • 13
    Electronic Resource
    Electronic Resource
    Synthesis and Reactions of Cyanic Esters (1967)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 6 (1967), S. 206-218 
    Details
    ISSN: 0570-0833
    Keywords: Cyanic esters ; Esters ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In 1963, it was found that sterically unhindered esters of cyanic acid, which had previously been considered unobtainable, could be easily prepared from phenols and cyanogen halides. Another synthesis, involving the thermolysis of thiatriazole derivatives, was discovered in 1964. The aryl cyanates in particular have since been found to have many uses as starting materials for the preparation of numerous new classes of compounds [e.g. derivatives of esters of imidocarbonic acid (esters, amides, imides, hydrazides, hydroxylamides, sulfamides, sulfhydrazides, semicarbazides); esters of imidocarboxylic acids; s-triazines, pyrimidines, tetrazoles, triazoles, triazolones, oxadiazoles, thiadiazoles, benzoxazinones, etc.], mainly by addition of nucleophilic or 1,3-dipolar reactants, or as aids e.g. in the elimination of H2O or H2S or in the transfer of CN groups.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196702061
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  • 14
    Electronic Resource
    Electronic Resource
    Syntheses of Thiocarbamates (1967)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 6 (1967), S. 281-293 
    Details
    ISSN: 0570-0833
    Keywords: Thiocarbamates ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The methods suitable for the preparation of thiocarbamates are described and illustrated by examples and procedures. They are grouped under the following headings:1Addition of Alcohols and Thiols to Isothiocyanates2Thioacylation of Amines(a)with chlorothioformates(b)with O,S-diesters of dithiocarbonic acid(c)with trithiocarbonates3Thioacylation of Alcohols, Phenols, and Thiols(a)with thiocarbamoyl chlorides(b)with N,N-dialkylmercaptochloroformimidium chlorides(c)with N,N′-thiocarbonyldiimidazole4Reaction of Thiocyanates and Cyanates with Hydrogen Sulfide5Alkylation of Metal Dithiocarbamates6Additions to Thiocyanic Acid
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196702811
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  • 15
    Electronic Resource
    Electronic Resource
    The Formation of C—C Bonds with the Aid of α-Halogeno Ethers, Sulfides, and AminesPart 30 of α-Halogenoether; Part 29: H. Gross, J. Gloede, and J. Freiberg, Liebigs Ann. Chem., 702, 68 (1967).Dedicated to Professor Alfred Rieche on the occasion of his 65th birthday (1967)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 6 (1967), S. 335-355 
    Details
    ISSN: 0570-0833
    Keywords: α-Halogeno ethers ; Ethers ; Sulfides ; Amines ; C-C coupling ; α-Halogeno amines ; Synthetic methods ; α-Halogeno sulfides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: α-Halogeno ethers, sulfides, and amines are reactive compounds which can be used for the formation of new C—C bonds, either as nucleophilic or as electrophilic reagents, or by α-elimination. The use of these compounds in the synthesis of many classes of organic compounds is reviewed.
    Additional Material: 14 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196703351
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  • 16
    Electronic Resource
    Electronic Resource
    Syntheses of Isocyanide DihalidesThe articles in this series have been published in five volumes by Verlag Chemie, Weinheim/Bergstr. An English edition has also been published. The present article will appear in Volume VI of the series. (1967)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 6 (1967), S. 649-665 
    Details
    ISSN: 0570-0833
    Keywords: Isocyanide dihalides ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The methods for the preparation of isocyanide dihalides, and particularly of isocyanide dichlorides, are described. The scopes and courses of the various processes are critically discussed.
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196706491
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  • 17
    Electronic Resource
    Electronic Resource
    New Methods of Preparative Organic ChemistryThe articles in this series have been published in five volumes by Verlag Chemie, Weinheim/Bergstrasse. An English edition has also been published. The present article, together with procedures will appear in Volume VI of the series.. Transfer of Diazo GroupsXIIIth report on reactions of compounds containing active methylene groups with azides. From the Habilitation Thesis of M. Regitz, Universität des Saarlandes, Saarbrücken, 1965; supplemented by more recent work. (1967)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 6 (1967), S. 733-749 
    Details
    ISSN: 0570-0833
    Keywords: Diazo group transfer ; Diazo compounds ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: When an arenesulfonyl azide, particularly p-toluenesulfonyl azide, reacts, in the presence of a base, with a compound containing an active methylene group, the two hydrogen atoms of the active methylene group are replaced by a diazo group to form a diazo compound and an arenesulfonamide. The method may be used for the synthesis of the diazo derivatives of cyclopentadienes, cyclohexadienes, 1,3-dicarbonyl, 1,3-disulfonyl, and 1,3-ketosulfonyl compounds, ketones, carbonic acid esters, and β-iminoketones. Secondary reactions can lead to azo compounds and heterocycles such as 1,2,3-triazoles, 1,2,3-thiadiazoles, and pyrazolin-4-ones. Azidinium salts react in the same way, but in this case an acidic reaction medium is necessary, a fact that is sometimes advantageous.
    Additional Material: 11 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196707331
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  • 18
    Electronic Resource
    Electronic Resource
    Spatial Arrangement and Preparative Organic Synthesis (1967)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 6 (1967), S. 778-789 
    Details
    ISSN: 0570-0833
    Keywords: Spatial arrangement ; Synthetic methods ; Stereochemistry ; Asymmetric synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: This review deals with the stereoselective formation of organic compounds. A number of examples of such syntheses, especially those of alkaloids and steroids, are described. An asymmetric synthesis, which avoids the intricacies and wastefulness of optical resolution, has been successful in a few cases only. The procedures of configurational change and of optical resolution, as well as the planning of multi-step stereoselective syntheses, are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196707781
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  • 19
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    Isonitrile Syntheses (1965)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 4 (1965), S. 472-484 
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    ISSN: 0570-0833
    Keywords: Formamides ; Synthetic methods ; Isocyanides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In spite of the large number of reactions which involve the formation of isonitriles, the only preparative routes to these compounds, until recently, were the classical isonitrile syntheses discovered about one hundred years ago by Gautier and Hofmann. These methods are not generally applicable, and give satisfactory yields only in exceptional cases. Isonitriles have recently become readily available by the elimination of water from N-substituted formamides, using acyl halides of Group IV-;VI elements in the presence of bases as dehydrating agents. A dehydrating system with a particularly wide range of application consists of phosgene with tertiary amines. This system generally provides the easiest and most productive route to isonitriles, particularly where large quantities (〉 1 mole) are to be prepared.
    Additional Material: 1 Tab.
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    URL: http://dx.doi.org/10.1002/anie.196504721
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  • 20
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    New Reactions of Alkylidenephosphoranes and their Preparative Uses. Part I: The Acid-Base Character of Phosphonium Salts and AlkylidenephosphoranesParts II and III will appear shortly in this journal. (1965)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 4 (1965), S. 583-587 
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    ISSN: 0570-0833
    Keywords: Alkylidenephosphoranes ; Phosphonium salts ; Synthetic methods ; Phosphoranes ; Ylides ; Alkenes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Phosphonium salts may be regarded as Bronsted acids, and alkylidenephosphoranes as the conjugate bases. Compounds of the two classes exist in equilibrium with each other. Phosphonium salts and alkylidenephosphoranes can be obtained by this “transylidation”. Other methods are also given for the preparation of members of both classes.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196505831
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  • 21
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    New Reactions of Alkylidenephosphoranes and their Preparative Uses. Part II. Alkylidenephosphoranes and Halogen CompoundsFor Part I see Angew. Chem. 77,609 (1965), Angew. Chem. internat. Edit. 4, 583 (1965). Part III will appear shortly in this journal. (1965)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 4 (1965), S. 645-660 
    Details
    ISSN: 0570-0833
    Keywords: Alkylidenephosphoranes ; Phosphonium salts ; Synthetic methods ; Phosphoranes ; Ylides ; Alkenes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of alkylidenephosphoranes with compounds containing halogens can be used to prepare ylides, which can be converted in to useful products, e.g. by hydrolysis, by thermal decomposition, or by other reactions. Examples of such products are ketones including cyclic, unsaturated, and branched-chain ketones (including cyclic, unsaturated, and branched-chain ketones), carboxlic esters (including those of unsaturated, branched- chain, polyenecarboxylic, acetylenecarboxylic, and allenecarboxylic acids), and aldehydes.
    Additional Material: 10 Tab.
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    URL: http://dx.doi.org/10.1002/anie.196506451
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  • 22
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    New Reactions of Alkylidenephosphoranes and their Preparative Uses IIIFor Part I, see Angew. Chem. 77, 609 (1965) Angew. Chem. internat. Edit. 4, 583 (1965); for Part II, see Angew. Chem. 77, 651 (1965); Angew. Chem. internat. Edit. 4, 645 (1965).. Alkylidenephosphoranes and Reagents Containing Multiple Bonds (1965)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 4 (1965), S. 830-838 
    Details
    ISSN: 0570-0833
    Keywords: Alkylidenephosphoranes ; Phosphonium salts ; Synthetic methods ; Phosphoranes ; Ylides ; Alkenes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A few examples of preparatively useful syntheses using alkylidenephosphoranes and substances containing a C—N or C—C double bond are the preparations of olefins, allenes, pyran derivatives, and cyclopropane derivatives. Olefins, ketones, and monocyclic compounds can be obtained by autoxidation of alkylidenephosphoranes; α, β-dioxo compounds (including cyclicones) can be prepared by oxidation with peroxy-acids. Alkylidenephosphoranes can also be used for the synthesis of azines and Schiff bases. Of the many possibilities offered by the Wittig reaction, only the preparation of tritiated aldehydes and olefins will be considered.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196508301
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  • 23
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    The Use of Silylation in Organic SynthesesThe articles of the previous three series have been collected and published in three volumes in German by Verlag Chemie, Weinheim, Bergstr. (Germany); and in English by Academic Press, New York-London. (1965)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 4 (1965), S. 417-429 
    Details
    ISSN: 0570-0833
    Keywords: Silylation ; Synthetic methods ; Trimethylsilyl group ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The term silylation is used to denote the introduction of a triorganosilyl moiety, especially the trimethylsilyl species, into organic compounds. - Silylated amino acids and sugars are particularly suitable for the syntheses of peptides and saccharides, respectively, since the silyl group can be cleaved off readily under mild conditions. Many diamines undergo ring closure, e.g. with phosgene, only after silylation. - O-silylated lactim ethers (i.e. cyclic imino ethers) are converted into N-alkyl derivatives by alkyl halides. Compounds with a strongly polarized Si—C bond may be used for chain extension. Silyl esters of halogeno fatty acids yield lactones with silver cyanate. - Trimethylsilyl azide is thermally very stable and behaves like organic azides. It reacts with acetylenic compounds, trialkylphosphines, and triarylphosphines to yield silylated triazole derivatives, trialkylphosphines N-silylimines, and triarylphosphines to yield silylated triazole dervatives, trialkylphosphine N-silylimines, and triarylphosphine N-silylimines, respectively, from which the silyl groups can be removed under mild conditions.
    Additional Material: 5 Tab.
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    URL: http://dx.doi.org/10.1002/anie.196504171
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