Indium(III) Chloride-Promoted Rearrangement of Epoxides: A Selective Synthesis of Substituted Benzylic Aldehydes and Ketones
The Journal of Organic Chemistry1998Vol. 63(23), pp. 8212–8216
Citations Over TimeTop 10% of 1998 papers
Abstract
A simple and efficient procedure for the rearrangement of substituted epoxides catalyzed by InCl3 has been developed. Aryl-substituted epoxides isomerize with complete regioselectivity to form a single carbonyl compound via cleavage of the benzylic C−O bond. The reactions are simple, fast, and high yielding. This procedure is very mild compared to those catalyzed with BF3 and other Lewis acids and compatible with several acid-sensitive functionalities. This protocol provides a highly selective synthesis of substituted benzylic aldehydes and ketones. However, rearrangement of alkyl-substituted epoxides is not very selective.
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