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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 179, 2004 - Issue 3
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Original Articles

MICROWAVE INDUCED SYNTHESIS OF COUMARINS FROM IN SITU GENERATED STABILIZED PHOSPHORUS YLIDES IN THE PRESENCE OF SILICA GEL POWDER IN SOLVENT-FREE CONDITIONS

Ali Ramazani Zanjan University, Zanjan, Iran
&
Ali Souldozi Zanjan University, Zanjan, Iran
Pages 529-533 | Received 01 Sep 2003, Published online: 12 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 phenols (1-hydroxynaphthalene, 2-hydroxynaphthalene and 4-bromophenol) leads to vinyltriphenylphosphonium salts, which undergo aromatic electrophilic substitution reaction with conjugate base to produce corresponding stabilized phosphorus ylides. Microwave was found to catalyze conversion of the stabilized phosphorus ylides to corresponding coumarins in the presence of silica gel powder in solvent-free conditions.

This work was supported by the Zanjan University.

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