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Olefination with Sulfonyl Halides and Esters: Scope, Limitations, and Mechanistic Studies of the Hawkins Reaction.

Bartosz Górski, Alicja Talko, Tymoteusz Basak, Michał Barbasiewicz
Organic Letters 2017 April 8
Carbanions of alkanesulfonyl halides and esters react with nonenolizable carbonyl compounds to give olefins. Mechanistic studies reveal that initial aldol-type addition of the carbanions is followed by cyclization-fragmentation to alkenes, and the leaving group on the sulfonyl moiety (RSO2 X) controls carbanion stability and rate of the olefin formation.

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