Sulfur dioxide promotes its hetero-Diels-Alder and cheletropic additions to 1, 2-dimethylidenecyclohexane

…, JA Sordo, F Monnat, B Deguin, P Vogel

Index: Fernandez; Sordo; Monnat; Deguin; Vogel Journal of the American Chemical Society, 1998 , vol. 120, # 50 p. 13276 - 13277

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Citation Number: 19

Abstract

Simple 1, 3-dienes add to SO2 in the presence of acid catalysts to generate the corresponding 3, 6-dihydro-1, 2-oxathiin-2-oxides (sultines) 1 at low temperature. This observation led us to invent a new carbon-carbon bond forming reaction in which electronrich dienes are condensed with electron-rich alkenes giving sulfinic acids that undergo stereoselective retro-ene elimination of SO2. Polypropionate fragments ...