Photooxidation of alkyl 4-nitrophenyl sulfides and sulfoxides. Observation of oxidative CS bond cleavage and rearrangement reactions

DJ Pasto, F Cottard, L Jumelle

Index: Pasto, Daniel J.; Cottard, Francois; Jumelle, Laurent Journal of the American Chemical Society, 1994 , vol. 116, # 20 p. 8978 - 8984

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Citation Number: 27

Abstract

Abstract: Alkyl 4-nitrophenyl sulfides and sulfoxides undergo a self-photoinduced, singlet oxygen oxidation to produce a variety of products, including sulfonates and carbonyl compounds formed by the oxidative cleavage of the CS bond of the sulfides and sulfoxides. Structural rearrangements are observed in the resulting carbonyl compounds formed in the oxidative cleavage of the CS bond in the tert-amyl and 2-phenylethyl sulfides. An overall ...