Bleach/acetic acid-promoted chlorinative ring expansion of [2.2.1]- and [2.2.2]-bicycles.

Org Lett

Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.

Published: October 2002

[formula: see text] Treatment of vinyl-substituted [2.2.1]- and [2.2.2]-bicyclocarbinols with NaOCl and AcOH provides [3.2.1]- and [3.2.2]-beta-chloro-bicycloketones, respectively. For [2.2.2]-bicycles, these chlorinative ring expansions are particularly efficient and selective.

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http://dx.doi.org/10.1021/ol0267331DOI Listing

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