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  • Wiley-Blackwell  (3)
  • 1
    Electronic Resource
    Electronic Resource
    Electron-Transfer-Catalyzed cis → trans Isomerization of 1,1′-AzonorboraneElectron-Transfer-Catalyzed Reactions, Part 11. Part I: [2].. Prototype of a reversible two-stage storage system (1992)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 75 (1992), S. 1607-1612 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ESR and cyclic voltammetry investigations show that isomerization of the radical cation of cis-1,1′-azonorbornane (cis-1) to the trans-radical ion proceeds too fast in solution for direct investigation of the cis-radical ion even at -78°. The facile isomerization of the radical cation is in agreement with PM3 calculations proposing an activation barrier of only 17 kJ/mol. As a consequence, quantitative cis → trans isomerization of 1,1′-azonorbornane can effectively be accomplished by addition of catalytic amounts of one-electron oxidants. This is the first evidence for a radical-cation-catalyzed cis → trans isomerization of azo compounds.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19920750515
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  • 2
    Electronic Resource
    Electronic Resource
    Formation of δ-Sultines (1,2-Oxathiane 2-Oxides) from Thiolane 1-Oxides (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 943-947 
    Details
    ISSN: 1434-193X
    Keywords: Thiolane 1-oxides ; Oxidations ; δ-Sultines ; [Bis(trifluoroacetoxy)iodo]benzene ; Asymmetric synthesis ; Carbanions ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -2-(Alkylthio)-2-benzylthiolane 1-oxides (1a, b) and 2-(alkylthio)-2-(α-hydroxybenzyl)thiolane 1-oxides (1c, d) are oxidized with [bis(trifluoroacetoxy)iodo]benzene (PIFA). Under ring enlargement the corresponding cyclic sulfinate esters (δ-sultines) 2 are formed. Only (1R*,2S*)-1b is reactive whereas (1R*,2R*)-1b is not attacked. This observation is explained with the formation of a cyclic intermediate 3.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Reaction of the Carbanions of 2-(Alkylthio)thiolane 1-Oxides with Oxiranes (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1481-1488 
    Details
    ISSN: 1434-193X
    Keywords: Thiolane 1-oxides ; Carbanions ; Oxiranes ; Asymmetric synthesis ; X-ray structure ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Carbanions of the 2-(alkylthio)thiolane 1-oxides 1 and 2 are generated and subjected to reaction with the epoxides 3-5. The resulting carbinols 6-11 are formed with high α diastereoselectivity, which is explained by a stabilization of the trans configuration of the carbanions in the activated complex. A minor γ stereoselectivity is also observed in case of the reactions with 4 and 5. The pure enantiomers (1S,2S,2′S)-9a and (1R,2R,2′S)-11b were obtained from 2 and (S)-4 or (R)-5, respectively, and their configurations were proved by X-ray structural analyses.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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