The Journal of organic chemistry

Economical and Environmentally Friendly Syntheses of 2-(Phenylsulfonyl)-1, 3-cyclohexadiene and 2-(Phenylsulfonyl)-1, 3-cycloheptadiene1

DJ Meyers, PL Fuchs

Index: Meyers, David J.; Fuchs, Philip L. Journal of Organic Chemistry, 2002 , vol. 67, # 1 p. 200 - 204

Full Text: HTML

Citation Number: 17

Abstract

The original synthetic plan involved conversion of the cyclic ketone to the enol thioether, followed by regioselective bromination. Oxidation of the corresponding phenyl sulfide to sulfone would then activate a base-catalyzed 1,4-elimination to yield the 2-substituted 1,3-diene. Numerous methods for the transformation of ketones to vinyl sulfides exist, but they involve multiple steps, corrosive Lewis acids, or moisture-sensitive anhydrides as reagents. Labiad found ...