LETTER	Synlett 2006: 1100-1104   DOI: 10.1055/s-2006-939692
© Georg Thieme Verlag Stuttgart · New York
Selenoxides as Catalysts for Epoxidation and Baeyer-Villiger Oxidation with Hydrogen Peroxide
Margaret A. Goodman, Michael R. Detty*
Department of Chemistry, University at Buffalo, The State University of New York, 627 Natural Sciences Complex, North Campus, Buffalo, New York 14260, USA Fax: +1(716)6456963; e-Mail: mdetty@buffalo.edu;
Received 14 February 2006

Abstract

Aryl benzyl selenoxides are catalysts for the epoxidation of various olefinic substrates and the Baeyer-Villiger oxidation of aldehydes and ketones with H₂O₂ in CH₂Cl₂ at 2.5 mol% catalyst. Benzyl 3,5-bis(trifluoromethyl)phenyl selenoxide (4) was the most effective catalyst while 2-(dimethylamino)phenyl benzyl selen­oxide was the least. Mono-, di-, and trisubstituted alkenes were ­epoxidized and adamantanone, cyclohexanone, and 3,4,5-trimethoxybenzaldehyde underwent Baeyer-Villiger oxidation using 4 and H₂O₂. Competition studies showed that epoxidation reactions were faster than Baeyer-Villiger oxidations although the selectivity varied only from 1.3:1 to 4.6:1.

Key words

catalysis - epoxidations - esters - oxidations - selenoxide