Abstract
The thero-anti-Markownikoff and threo-Markownikoff adducts are the products of addition of 4-chloro-and 2,4-dinitrobenzenesulfenyl chloride to cis-1-phenylpropene while only the erythro Markownikoff adduct is the product of addition to trans-1-phenylpropene. The addition reaction follows second order kinetics, first order in both olefin and arylsulfenyl chloride, with the rate of addition to the trans-olefin faster than to the cis. These results are consistent with a mechanism involving bridged transition states in both the rate and product determining steps.
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