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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 182, 2007 - Issue 2
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Original Articles

Three-Component Reaction of Triphenylphosphine, Acetylenic Esters, and Aromatic Amides: The Synthesis of Stable Nitrogen-Containing Phosphorus Ylides

Mohammad Anary-Abbasinejad Department of Chemistry, Islamic Azad University, Yazd Branch, Yazd, Iran
&
Sakkineh Tahhan Department of Chemistry, Islamic Azad University, Yazd Branch, Yazd, Iran
Pages 315-319 | Received 18 Aug 2005, Accepted 07 Jul 2006, Published online: 18 Feb 2007
 
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Abstract

Protonation of the reactive 1:1 intermediate produced in the reaction between dialkyl acetylenedicarboxylates and triphenylphosphine by aromatic amides leads to vinylphosphonium salts, which undergo a Michael addition with the conjugate base of the amide to produce highly functionalized, salt-free phosphorus ylides in good yields.

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