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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 1-2
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Original Articles

Potassium Bromide/m-Chloroperbenzoic Acid/18-Crown-6. A Convenient Reagent for the Preparation of trans 1,2-Bromocarboxylates

Morris Srebnik Department of Natural Products, Faculty of Medicine, Hebrew University, Jerusalem, Israel; Department of Chemistry, Purdue University, West Lafayette, Indiana, 47907
Pages 197-205 | Received 13 May 1988, Published online: 24 Oct 2006
 
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Abstract

In the presence of 18-crown-6 (10 mmol%), potassium bromide reacts with m-CIPBA to form m-chlorobenzoylhypobromite. The latter readily adds across carbon-carbon double bonds to furnish 1,2-bromocarboxylates in a highly regio- and stereospecific manner.

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