Regiochemical and stereochemical studies on halogen-induced ring expansions of unsaturated episulfides

…, MI Konaklieva, E Turos, LM Krajkowski…

Index: Ren, Xiao-Feng; Konaklieva, Monika I.; Turos, Edward; Krajkowski, Lynn M.; Lake, Charles H.; et al. Journal of Organic Chemistry, 1995 , vol. 60, # 20 p. 6484 - 6495

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Citation Number: 15

Abstract

The reactions of unsaturated episulfides with bromine and iodine have been studied. Initially produced in the reaction is a ring-opened sulfenyl halide intermediate, which in the presence of the carbon-carbon double bond or triple bond cyclizes to P, P-dihalo sulfide cycloadducts. The regiochemistry and relative stereochemistry of these cyclizations have been examined as a function of the length of the tether between the episulfide moiety and ...