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  • 1
    Electronic Resource
    Electronic Resource
    Elektroreduktion organischer Verbindungen, 16. Elektroreduktion von ω-Halogenalkandithiosäure-methylestern (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 1733-1737 
    Details
    ISSN: 0009-2940
    Keywords: Dithiolactones ; Electroreduction ; Haloalkanedithioates ; Thioacetals, semicyclic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Intramolecular cyclization occurs on electroreduction of the methyl -haloalkanedithioates 1 in methanol. The expected semicyclic thioacetals 2 are formed according to an ECEH mechanism. The biheterocycles 12 result from dimerization of intermediate radicals whereas the semicyclic ketene dithio-acetals 13 are formed by non-electrochemical processes. The 2-(methylthio)thiolanes 2 a and 16 are obtained with much higher yields and better selectivity by co-electroreduction of the -dithio-lactones 15 in the presence of dimethyl sulfate.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230825
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    C,C-Verknüpfungen mit Schwefel-stabilisierten Carbanionen, 2[1] Reaktionen des 2-(Methylthio)thiolan-Carbanions mit Elektrophilen[2] (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 1641-1646 
    Details
    ISSN: 0009-2940
    Keywords: Thioacetals, semicyclic ; Carbanions ; Alkylation ; Hydroxyalkylation ; Diastereoselectivity ; Thiolanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: C,C Coupling with Sulfur-Stabilized Carbanions, 2[1]. - Reactions of the 2-(Methylthio)thiolane Carbanion with Electrophiles[2]The „semicyclic” thioacetal 2-(methylthio)thiolane (4) is easily prepared from thiolane (tetrahydrothiophene). It is readily deprotonated by butyllithium to give the lithium derivative 5, which reacts with alkyl halides, saturated and α,β-unsaturated carbonyl compounds, and benzonitrile to form the alkyl derivatives 6, carbinols 7, allyl alcohols 8, and - after hydrolysis - the ketone 9. The diastereoselectivity of the C,C coupling reaction is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250720
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    Paper (German National Licenses)
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