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Synthesis 2014; 46(02): 251-257
DOI: 10.1055/s-0033-1340298
DOI: 10.1055/s-0033-1340298
paper
Vicinal Dichlorination of Olefins Using NH4Cl and Oxone®
Further Information
Publication History
Received: 28 August 2013
Accepted after revision: 29 October 2013
Publication Date:
28 November 2013 (online)
Abstract
A mild and efficient protocol for the preparation of 1,2-dichloroalkane derivatives from olefins using NH4Cl and Oxone® at room temperature is described. A variety of terminal, internal, and cyclic alkenes reacted smoothly to give the corresponding dichlorinated products in good to excellent yields. Moreover, 1,2-disubstituted symmetrical and unsymmetrical olefins dichlorinated with moderate to excellent diastereoselectivity. This method precludes the use of acidic additives and transition metals in the synthesis of vicinal dichlorides.
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- Supporting Information
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For pioneering studies on this class of molecules, see: