Journal of the American Chemical Society

Factors influencing the nature of the episulfonium ion in sulfenyl chloride addition to terminal olefins

WH Mueller, PE Butler

Index: Mueller,W.H.; Butler,P.E. Journal of the American Chemical Society, 1968 , vol. 90, # 8 p. 2075 - 2081

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Citation Number: 118

Abstract

Abstract: Methane-and benzenesulfenyl chloride afforded predominantly anti-Markovnikov oriented adducts with terminal alkyl substituted olefins and vinyl chloride. This adduct selectivity increased with increasing bulki-ness of the alkyl substituent of the substrate. These kinetically controlled adducts were found to readily undergo acid-catalyzed isomerization to the thermodynamically more stable Markovnikov adducts. Phenyl ...