SYNTHESIS OF HIGHLY ELECTRON-POOR ALKENES FROM IN SITU GENERATED STABILIZED PHOSPHORUS YLIDES AND NINHYDRIN VIA INTERMOLECULAR WITTIG REACTION

Author: Ramazani Ali   Bodaghi Ali  

Publisher: Taylor & Francis Ltd

ISSN: 1042-6507

Source: Phosphorus, Sulfur, and Silicon and the Related Elements, Vol.179, Iss.8, 2004-01, pp. : 1615-1620

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Abstract

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by alcohols leads to vinyltriphenylphosphonium salts, which undergo Michael addition reaction with conjugate base to produce the corresponding stabilized phosphorus ylides. Intermolecular Wittig reaction of the stabilized phosphorus ylides with ninhydrin leads to the corresponding, highly electron-poor alkenes.

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