Tetrachlorovinylcarbene from Tetrachlorocyclopropene; Facile Synthesis of Vinylcyclopropanes

Authors

  • Dipl.-Chem. Walter Weber,

    1. Institut für Organische Chemie und Biochemie der Universität, Martin-Luther-King-Platz 6, D-2000 Hamburg 13
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  • Prof. Dr. Armin de Meijere

    Corresponding author
    1. Institut für Organische Chemie und Biochemie der Universität, Martin-Luther-King-Platz 6, D-2000 Hamburg 13
    • Institut für Organische Chemie und Biochemie der Universität, Martin-Luther-King-Platz 6, D-2000 Hamburg 13
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  • This work was supported by the Fonds der Chemischen Industrie, Hoechst AG, and the Hermann-Schlosser-Stiftung.

  • Dedicated to Professor Rolf Sammet on the occation of his 60th birthday

Abstract

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Tetrachlorovinylcarbene, Cl[BOND][BOND]CCl[DOUBLE BOND]CCl2, is unexpectedly formed on reaction of tetrachlorocyclopropene (1) with alkenes (2), in which the adducts (3) can be isolated. As shown by numerous examples, this type of reaction can be generalized, e.g. for synthesis of acids and esters (3), R1 = CO2H and CO2R, having potential as insecticides.

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