Tributylstannane-mediated cyclization of thionocarboxylic acid derivatives

…, E Bosch, D Denenmark, D Girsh

Index: Bacchi, Mario D.; Bosch, Eric; Denenmark, Daniella; Girsh, Diana Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6803 - 6810

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Citation Number: 32

Abstract

Cyclization reactions of various thionoestera and thioamides involving the addition of tri-n- butylstannyl radical to a thiocarbonyl group and intramolecular addition of the resulting radical to a carbon-carbon multiple bond was studied. Dithiocarbonate and (imidazoly1) thiocarbonyl derivatives of homoallylic alcohols gave a-substituted ythionobutyrolactones. The reaction is highly dependent on the substitution pattern on the double bond, a high ...