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Anomalous formation of 1,1,4-tribromohex-1-en-3-one in the wittig reaction of 2-halopent-2-enals with dibromomethylene triphenylphosphorane

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
24
Issue
32
Identifiers
DOI: 10.1016/s0040-4039(00)86278-4

Abstract

Abstract The heretofore unreported Wittig reaction of 2-halopent-2-enals with dibromomethylene triphenylphosphorane yields variable amounts of 1,1,4-tribromohex-1-en-3-one and/or the expected dienes according to the substrate and reaction conditions. A plausible mechanism to rationalize the unforeseen formation of this ketone is discussed.

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