Synthesis of Nitriles via the Ylide Anion of Sodium Cyanotriphenylphosphoranylidenemethanide

Authors

  • Prof. Dr. Hans Jüryen Bestmann,

    Corresponding author
    1. Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)
    • Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)
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  • Dipl.-Chem. Martin Schmidt

    1. Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)
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Abstract

original image

A convenient access to nitriles having a variety of extremely different structures is provided by the ylide anion 1, which is isolable as the sodium salt. By reaction with alkyl halides RX, 1 can be converted into cyclic α,β-unsatu-rated nitriles such as 2; the “dienyl cyanides” 3 and alkynyl cyanides R[BOND]C[TRIPLE BOND]C[BOND]CN are obtainable from 1 by reaction with aldehydes RCHO and esters RCOOR', respectively.

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