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A Novel Procedure for the Synthesis of Epoxides: Application of Simmons-Smith Reagents toward Epoxidation

Varinder K. Aggarwal, Amjad Ali and Michael P. Coogan

*School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK, Email:

V. K. Aggarwal, A. Ali, M. P. Coogan, J. Org. Chem., 1997, 125, 8628-8629.

DOI: 10.1021/jo971773h


A novel application of organozinc reagents toward the epoxidation of carbonyl compounds via the intermediacy of sulfur ylides has been developed.

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Reaction Pathway

Developments in the Simmons-Smith-Mediated Epoxidation Reaction

V. K. Aggarwal, M. P. Coogan, R. A. Stenson, Ra. V. H. Jones, R. Fieldhouse, J. Blacker, Eur. J. Org. Chem., 2002, 319-326.

DOI: 10.1002/1099-0690(20021)2002:2<319::AID-EJOC319>3.0.CO;2-R

Key Words

Sulfonium Ylides, Epoxides, Corey-Chaykovsky Reaction

ID: J48-Y2003-1680