Synthesis and Reactions of Stabilized Phosphorus Ylides

Title: Synthesis and Reactions of Stabilized Phosphorus Ylides

Volume: 12 Issue: 1

Author(s): Ali Ramazani, Ali Reza Kazemizadeh, Ebrahim Ahmadi, Nader Noshiranzadeh and Ali Souldozi

Affiliation:

Keywords: dialkyl acetylenedicarboxylates, organophosphorus compounds, Protonation, Quinolines, Wittig reaction

Abstract: Stabilized phosphorus ylides, versatile intermediates in synthetic organic chemistry can be prepared by the novel reaction of dialkyl acetylenedicarboxylates (DAAD), triphenylphosphine (TPP) and acids such as phenols, imides, amides, enols, oximes and alcohols. The reaction involves an intermediate formed by the 1:1 conjugate addition reaction of the TPP to DAAD and concomitant protonation of the intermediate by an acid leads to vinyltriphenylphosphonium salts. The salts are unstable intermediates and converted to stabilized phosphorus ylides via Michael addition reaction. The stabilized phosphorus ylides are able to take part in the normal intramolecular Wittig reactions but they are not generally able to participate in the normal intermolecular Wittig reactions. The intermolecular Wittig reactions of the ylides are observed only with highly electron-poor carbonyl groups such as indane-1,2,3-trione. The ylides are converted to electron-poor alkenes via elimination of TPP in solvent-free conditions. Almost all of the final products are valuable families of compounds.

Cite this article as:

Ramazani Ali, Kazemizadeh Reza Ali, Ahmadi Ebrahim, Noshiranzadeh Nader and Souldozi Ali, Synthesis and Reactions of Stabilized Phosphorus Ylides, Current Organic Chemistry 2008; 12 (1) . https://dx.doi.org/10.2174/138527208783330055