Journal of the American Chemical Society

New synthetic reactions. Stereoreversed cyclobutanone formation utilizing selenoxide as a leaving group

BM Trost, PH Scudder

Index: Trost,B.M.; Scudder,P.H. Journal of the American Chemical Society, 1977 , vol. 99, p. 7601 - 7610

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Citation Number: 37

Abstract

Abstract: Oxaspiropentanes undergo smooth opening with sodium phenylselenide in ethanol to give the P-hydroxyselenides at room temperature. Oxidation with m- chloroperbenzoic acid at-78 to-30 OC and rearrangement at-30" C in the presence of pyridine leads directly to cyclobutanones. A mechanism invoking benzeneselenenate as a leaving group to generate a carbonium ion is presented. The stereochemistry is ...