Substituent effects on the photocleavage of benzyl-sulfur bonds. Observation of the “Meta Effect”

SA Fleming, AW Jensen

Index: Fleming, Steven A.; Jensen, Anton W. Journal of Organic Chemistry, 1996 , vol. 61, # 20 p. 7040 - 7044

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Citation Number: 27

Abstract

Benzyl phenyl sulfide has been used to investigate the photocleavage mechanism for benzyl-sulfur bonds. Four experiments have shown that the reaction goes through a radical intermediate. First, the photoproducts observed can all be justified by radical mechanisms. Second, the radical intermediate was trapped with a five hexenyl tether. Third, UV analysis of analogs for the 4-NO2 derivative indicate no exciplex or electron transfer pathway. ...