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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 179, 2004 - Issue 8
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Original Articles

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

Ali Ramazani Chemistry Department, Zanjan University, Zanjan, Iran
&
Ali Bodaghi Chemistry Department, Zanjan University, Zanjan, Iran
Pages 1615-1620 | Received 01 Dec 2003, Published online: 16 Aug 2010
 
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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.

The Zanjan University Research Council supported this work.

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