Chloroacetylenes as Michael acceptors. 3. Mechanism and synthetic utility of enolate reactions with halogenated olefins and chloroacetylenes

AS Kende, P Fludzinski, JH Hill

Index: Kende,A.S.; Fludzinski,P.; Hill,J.H. Journal of the American Chemical Society, 1984 , vol. 106, p. 3551

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Citation Number: 70

Abstract

Abstract: Condensations of tertiary conjugated enolates with a variety of polyhalogenated olefins were explored. Trichloroethylene led to (E)-1, 2-dichlorovinyl adducts which could be further converted to acetylenes in good yield. 1, 2-Dichloro-1-fluoroethylene (1/1 cis/trans) led to a single regio-and stereoisomeric adduct ((E)-2-chloro-l-fluorovinyl) in 30% yield, whereas tetrachloroethylene led to a chloroethynyl adduct in 25% yield. Attempts to ...