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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

✍ Scribed by F. Camps; J. Coll; G. Fabriás; A. Guerrero; M. Riba

Book ID
104220126
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
232 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

The heretofore unreported Wittig reaction of Z-halopent-Z-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. Wittig reaction of aldehydes with dibromomethylene triphenylphosphorane is a well established procedure for preparation of l,l-dibromo olefins!

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