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
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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 ...
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