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Original Articles

CONVERSION OF IN SITU GENERATED STABILIZED PHOSPHORUS YLIDES TO CHROMENE DERIVATIVES IN SOLVENT-FREE CONDITIONS

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Pages 1459-1464 | Received 01 Nov 2003, Accepted 01 Nov 2003, Published online: 16 Aug 2010
 

Abstract

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by phenols (1-hydroxynaphthalene, 2-hydroxynaphthalene, 4-bromophenol, 2-hydroxybenzaldehyde, and 5-bromo-2-hydroxyben- zaldehyde) leads to vinyltriphenylphosphonium salts, which undergo electrophilic substitution reaction with conjugate base to produce corresponding stabilized phosphorus ylides. Microwave was found to catalyze conversion of the stabilized phosphorus ylides to chromene derivatives in the presence of solid catalysts in solvent-free conditions at microwave power 0.4 KW in 3 min.

The Zanjan University supported this work.

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