Phosphoryl-stabilized

Wadsworth, W.S., Synthetic applications of phosphoryl-stabilized anions, Org. React., 25, 73, 1977. 

Phosphoryl-stabilized anions, 25, 2 Photochemical cycloadditions, 44, 2 Photocyclization of stilbenes, 30, 1 Photooxygenation of olefins, 20, 2 Photosensitizers, 20, 2 Pictet-Spengler reaction, 6, 3 Pig liver esterase, 37, 1 Polonovski reaction, 39, 2... 

Wadsworth, W. S. Jr. Synthetic applications of phosphoryl-stabilized anions. In Dauben, W. G., Ed.-in-Chief "Organic Reactions", Vol. John Wiley Sons, Inc. New York, 1977 pp. 73-253. 

Maryanoff, B.E. and Reitz, A.B. (1989) The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects. Chemical Reviews, 89(4), 863-927. 

A convenient route to trivinylphosphine has been developed by thiol elimination from tris[2-(phenylthio)ethyl]phosphine oxide.56 The reaction mechanism involves a phosphoryl-stabilized carbanion, from which benzene thiolate anion is eliminated. 

W. S. Wadsworth, Jr., Synthetic Applications of Phosphoryl-Stabilized Anions, Org. React. 1977, 25, 73-253. 

For a summary of current work on the mechanism of phosphoryl-stabilized Wittig reactions as well as the preparation of these reagents, see ref. 114. 

HWE olefination Stereoselective olefination of aldehydes and ketones using phosphoryl-stabilized carbanions. 212... 

Arlamkina, G.A., Sazonov, P.K., and Beletskaya, I.P., Arylation of phosphoryl-stabilized carbanions with metal Jt-complexes of aryl chlorides and fluorides, Tetrahedron Lett., 42, 4385, 2001. 

Several innovations have significantly extended the scope and synthetic utility of the classical Michaelis-Becker phosphonoacetate preparation. Eor example, the coupling of the Michaelis-Becker and Homer-Wadsworth-Emmons reactions for the synthesis of a-substituted acrylic acids represents a useful modification. According to Scheme 8.10, Michaelis-Becker alkylation of a dialkyl phosphite with a haloacetic acid in the presence of 3 eq of a base (one to neutralize the carboxyl group, one to form the phosphite conjugate base, and one to deprotonate the initially formed alkylation product) leads to the phosphoryl-stabilized anion directly. Treatment of the anion... 

Y 22. Maryanoff. B.E. Reitz, A.B. The Wittig Olefination Reaction and Modifications Involving Phosphoryl-Stabilized Carbanions. Stereochemistry, Mechanism, and Selected Synthetic Aspects Chem Rev. 1989, 89, 863-927... 

The Wittig Olefination Reaction and Modifications Involving Phosphoryl-Stabilized Carbanions. Stereochemistry, Mechanism and Selected Synthetic Aspects"... 

The disadvantages of the Wittig reaction described in Section A led to the development of modified olefination methods based on phosphoryl-stabilized carbanions. The most important modification of the Wittig reaction in the field of carotenoid synthesis is olefination by means of phosphonate carbanions, as introduced by Homer [55] and by Wadsworth and Emmons [56]. 

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