Tetrahedron

One-pot synthesis of 1-aryl-3-methyl-1, 3-dienes using methallyl (trimethyl) silane and aldehydes and their low temperature (Z)→(E) isomerization induced by sulfur …

SR Dubbaka, P Vogel

Index: Dubbaka, Srinivas Reddy; Vogel, Pierre Tetrahedron, 2005 , vol. 61, # 6 p. 1523 - 1530

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Citation Number: 14

Abstract

2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1- sulfonyl fluorides give 1, 3-(E) and (Z)-dienes. Their (Z)→(E) isomerization by classical means fails or leads to their polymerization. It is shown that SO2 can isomerize 1-aryl-3- methyl-1, 3-dienes at low temperature, without formation of sulfolenes (cheletropic ...