89510-63-4Relevant academic research and scientific papers
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 dioxide
Dubbaka, Srinivas Reddy,Vogel, Pierre
, p. 1523 - 1530 (2007/10/03)
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 addition/elimination). Preliminary mechanistic studies suggest that SO2 adds to 1,3-dienes forming 1,4-diradical intermediates that are responsible for the (Z)→(E) isomerizations.
