Vicinal Dichlorination of Olefins Using NH₄Cl and Oxone®

Peraka Swamy, Marri Mahender Reddy, Macharla Arun Kumar, Mameda Naresh, Nama Narender*

*Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India, Email: narendern33yahoo.co.in

P. Swamy, M. M. Reddy, M. A. Kumar, M. Naresh, N. Narender, Synthesis, 2014, 46, 251-257.

DOI: 10.1055/s-0033-1340298

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Abstract

A mild and efficient protocol enables the preparation of 1,2-dichloroalkane derivatives from olefins in the presence of NH₄Cl and Oxone at room temperature. Various terminal, internal, and cyclic alkenes reacted smoothly to give the corresponding dichlorinated products in good to excellent yields. Internal olefins dichlorinated with moderate to excellent diastereoselectivity.

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Key Words

vicinal dichlorination, benzyl chlorides, olefins, Oxone, diastereoselectivity

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ID: J66-Y2014