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A novel rearrangement induced by the addition of organyllithium reagents to 2,3-difluoro-4,4-dimethylbut-2-enolide

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
35
Issue
49
Identifiers
DOI: 10.1016/0040-4039(94)88482-x

Abstract

Abstract Addition of O-nucleophiles and Grignard reagents in the presence of copper(I) bromide-dimethyl sulphide to 2,3-difluoro-4,4-dimethylbut-2-enolide proceeds by 1,4-addition and expulsion of a fluoride anion to give 4-substituted butenolides. Organolithium reagents, however, react to give furan(2H)-3-ones in a novel oxygen rearrangement reaction.

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