Enol thioethers as enol substitutes. An alkylation sequence

BM Trost, AC Lavoie

Index: Trost; Lavoie Journal of the American Chemical Society, 1983 , vol. 105, # 15 p. 5075 - 5090

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Citation Number: 184

Abstract

Abstract: Ionic bromination of enol phenyl thiolethers forms predominantly to exclusively 2- (phenylthio)-3-bromo-1-alkenes, an enolonium equivalent. The allylic bromide participates in displacements with stabilized and nonstabilized nucleophiles. The ability to hydrolyze the enol thioethers to their corresponding ketones equates this sequence to an equivalence of an enolonium ion. The versatility of the sulfur in selective introduction of allylic hydroxyl ...