Regioselective Conversion of Unsymmetrical Terminal Epoxides into Vicinal Chlorohydrins Using Dimethoxyboron Chloride

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Contents Vol 59(11)

doi:10.1071/CH06315

Regioselective Conversion of Unsymmetrical Terminal Epoxides into Vicinal Chlorohydrins Using Dimethoxyboron Chloride*

Chandra D. Roy

^A Department of Chemistry, Herbert C. Brown Center for Borane Research, Purdue University, West Lafayette, IN 47907, USA. Email: chandra0919@gmail.com
^B Present address: EMD Biosciences, Inc., 10394 Pacific Center Court, San Diego, CA 92121, USA.





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Australian Journal of Chemistry 59(11) 834–836 http://dx.doi.org/10.1071/CH06315
Submitted: 28 August 2006 Accepted: 1 October 2006 Published online: 17 November 2006

Abstract

A highly regioselective synthesis of chlorohydrins by chlorinative cleavage of unsymmetrical epoxides utilizing dimethoxyboron chloride is described. Except for styrene oxide, all the terminal epoxides were regioselectively cleaved following a predominantly S_N2-type reaction pathway favouring the formation of primary chlorides. In the case of styrene oxide, a benzylic epoxide, (MeO)₂BCl transfers the chlorine at the benzylic position, by following an apparent S_N1-type mechanism.

^* This paper is dedicated to the memory of my mentor, the late Professor Herbert C. Brown (1912–2004). The work described herein was carried out at Purdue University during my stay as a post-doctoral research associate (1995–2001).