Tandem photocyclization-intramolecular addition reactions of aryl vinyl sulfides. Observation of a novel [2+ 2] cycloaddition-allylic sulfide rearrangement

…, XY Nie, H Nie, H Ramanathan, C Buntel…

Index: Dittami, James P.; Nie, Xiao Yi; Nie, Hong; Ramanathan, H.; Buntel, C.; et al. Journal of Organic Chemistry, 1992 , vol. 57, # 4 p. 1151 - 1158

Full Text: HTML

Citation Number: 29

Abstract

Photocyclization of aryl vinyl sulfides reportedly proceeds via thiocarbonyl ylide intermediates. The photochemical behavior of several aryl vinyl sulfides, which incorporate a pendant alkene side chain, was explored. In general, naphthyl and phenyl vinyl thioethers provided products which are consistent with photocyclization to a thiocarbonyl ylide intermediate followed by either intramolecular hydrogen shift or subsequent ...