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  • Organic Chemistry  (2)
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  • 1
    Electronic Resource
    Electronic Resource
    Metallierte Stickstoffderivate der Kohlensäure in der organischen Synthese, XVI. Die Synthese von 2-Alkylimino- und 2-Arylimino-1,3-oxathiolanen aus lithiierten Imidodithiokohlensäure-S,S′-dialkylestern und Carbonylverbindungen (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1765-1778 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Metalated Nitrogen Derivatives of Carbonic Acid in Organic Synthesis, XVI.  -  Synthesis of 2-Alkylimino- and 2-Arylimino-1,3-oxathiolanes from Lithiated S,S′-Dialkyl Imidodithiocarbonates and Carbonyl CompoundsS,S′-Dialkyl N-(methyl)-, N-(phenyl)-, or N-(cyclopropyl)imidodithiocarbonates 5 were deprotonated by means of lithium diisopropylamide. The resulting α-thio-substituted lithium alkanides 6, which are stabilized by chelatization, were trapped as trimethylsilanes 7. Reaction of 6 with aldehydes or ketones yields the title compounds 20 via adducts 18 and loss of methanethiolate.
    Notes: N-(Methyl)-, N-(Phenyl)- oder N-(Cyclopropyl)imidodithiokohlensäure-S,S′-dialkylester 5 wurden mit Lithiumdiisopropylamid deprotoniert zu den Chelat-stabilisierten α-Thiolithiumalkaniden 6, welche als Silane 7 nachgewiesen wurden. Die Umsetzung von 6 mit Aldehyden und Ketonen liefert über die Addukte 18 unter Abspaltung von Methanthiolat die Titelverbindungen 20.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019801116
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  • 2
    Electronic Resource
    Electronic Resource
    Metallierte Stickstoffderivate der Kohlensäure in der organischen Synthese, XVII. Die Umwandlung von 2-Methylimino-1,3-oxathiolanen in Thiirane (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1779-1785 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Metalated Nitrogen Derivatives of Carbonic Acid in Organic Synthesis, XVII.  -  Conversion of 2-Methylimino-1,3-oxathiolanes into Thiiranes2-Methylimino-1,3-oxathiolanes 3, readily obtained from lithiated S,S′-dialkyl N-(methyl)imidodithiocarbonates 1 and carbonyl compounds 2, were transformed into thiiranes 6 via N,N-dimethyl-N-(1,3-oxathiolan-2-ylidene)ammonium iodides 7. With exclusion of 5-aryl-substituted compounds 3 the reaction proceeds highly diastereoselectively.
    Notes: Die 2-Methylimino-1,3-oxathiolane 3, erhalten aus den lithiierten N-(Methyl)imidodithiokohlensäure-S,S′-dialkylestern 1 und Carbonylverbindungen 2, wurden über N,N-Dimethyl-N-(1,3-oxathiolan-2-yliden)ammoniumiodide 7 in Thiirane 6 umgewandelt. Mit Ausnahme 5-arylsubstituierter Verbindungen 3 verläuft die Reaktion hochdiastereoselektiv unter Retention der Konfiguration.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019801117
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
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