Doubly Deprotonated Allylacetophenone. First Example of a “Direct” E5 Synthon

Authors

  • Manat Pohmakotr,

    M. Sc.
    1. Institut für Organische Chemie der Universität Giessen Heinrich-Buff-Ring 58, D-6300 Lahn-Giessen (Germany)
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  • Prof. Dr. Dieter Seebach

    Corresponding author
    1. Institut für Organische Chemie der Universität Giessen Heinrich-Buff-Ring 58, D-6300 Lahn-Giessen (Germany)
    Current affiliation:
    1. Laboratorium für Organische Chemie der ETH ETH-Zentrum, Universitätsstrasse 16, CH-8092 Zürich (Switzerland)
    • Institut für Organische Chemie der Universität Giessen Heinrich-Buff-Ring 58, D-6300 Lahn-Giessen (Germany)
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  • Part of the projected Doctoral Thesis by M. P., Universität Giessen.—M. P. wishes to thank the DAAD for a stipend. This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.

Abstract

original image

The first unsaturated carbonyl derivative to react at C-5 with electrophiles is the dianion (1). It forms adducts (2) or (3) which can be cyclized to tetrahydrofurans or- pyrans if they contain OH groups.

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