Sulfur as a regiochemical control element. Synthesis of 2-alkoxy (acyloxy)-3-alkyl (aryl) thiobuta-1, 3-dienes

…, WC Vladuchick, AJ Bridges

Index: Trost,B.M.; Vladuchick,W.C.; Bridges,A.J. Journal of the American Chemical Society, 1980 , vol. 102, p. 3548

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Citation Number: 45

Abstract

Abstract: The internal competition between substituents in the 2, 3 positions of a diene-one being a sulfur and the other an oxygen substituent-is discussed. To examine this question, a general approach to 2-alkoxy (acyloxy)-3-alkyl (aryl) thiobuta-I, 3-dienes has been developed. Bromocyclobutanone undergoes displacement with sulfur nucleophiles without competing rearrangements of the benzylic acid type. These compounds have been 0- ...