Tetrahedron Letters

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

F Camps, J Coll, G Fabrias, A Guerrero, M Riba

Index: Camps, F.; Coll, J.; Fabrias, G.; Guerrero, A.; Riba, M Tetrahedron Letters, 1983 , vol. 24, # 32 p. 3387 - 3390

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Citation Number: 11

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.