Preparation and reactions of 1-(phenylthio)-2-(trimethylsilyloxy)-1, 3-butadienes. A one-pot synthesis of sulfur-substituted 7-hydroxybicyclo [2.2. 1] heptanones- …

AP Kozikowski, EM Huie

Index: Kozikowski, Alan P.; Huie, Edward M. Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2923 - 2925

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Citation Number: 15

Abstract

5 S0 in acceptable overall yield from the alcohol formed on addition of lithiated thioanisole to metha~ rolein.~ The oxidation state of this alcohol was taken to the ketone level by use of the Swern procedure, and the resulting 3-methyl-l-(phenylthio)-3-buten-2-one was trimethylsilylated with TMSCl/Et3N/ZnC1: to produce stereospecifically (Z)-3-methyl-l- (phenylthio)-2-[(trimethyl-silyl) oxy]-1, 3-butadiene (la). Room-temperature Diels-Alder ...