The Journal of Organic Chemistry

A method for mild photochemical oxidation; conversion of phenacyl sulfides into carbonyl compounds

E Vedejs, DA Perry

Index: Vedejs, E.; Perry, D. A. Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 573 - 575

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Citation Number: 27

Abstract

Summary: Sunlamp irradiation of phenacyl sulfides PhCOCH2SCHRR'affords thiocarbonyl compounds S= CRR'that can be trapped in high yield by using the nitronate CH, CH= N+(OTBS) O-; the heterocycle 3 resulting from 1, 3-dipolar cycloaddition is cleaved rapidly by fluoride ion to give ketones or aldehydes.