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2005
Alkenes
Q 0083
22- 066
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. — (Z) → (E) isomerization of title compounds (IV) by established
methods is mentioned to fail or to furnish polymerized products. It can be achieved using SO2 at low temperature to avoid formation of sulfolenes. This isomerization is suggested to proceed via addition of SO2 to the 1,3-diene forming 1,4-diradical intermediates. — (DUBBAKA, S. R.; VOGEL*, P.; Tetrahedron 61 (2005) 6, 1523-1530; Lab.
Glycochem. Asymmetric Synth., Swiss Fed. Inst. Technol., CH-1015 Lausanne,
Switz.; Eng.) — Nuesgen
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