Synthesis by SO2 Extrusion: Photochemical and Thermal Reactions of Cinnamyl Benzyl Sulfone

Article abstract of DOI:10.1021/jo00170a029

The photochemistry and pyrolytic behavior of trans-cinnamyl benzyl sulfone have been investigated.Direct photolysis in benzene gives high yields of the SO2 extrusion products 3,4-diphenyl-1-butene and cis- and trans-1,4-diphenyl-1-butene.Addition of trans-piperylene to the photolysis substantially reduces the amount of cis-1,4-diphenyl-1-butene formed.Photolysis in acetone gives primarily trans-cis isomerization, though minor amounts of the SO2 extrusion products and bibenzyl were also formed.Flash vacuum pyrolysis of cinnamyl benzyl sulfone gave only minor amounts o f the SO2 extrusion products; these were shown to be unstable under the conditions of pyrolysis.Instead, indene, styrene, bibenzyl, and toluene were formed.Pyrolysis of 1,4-diphenyl-1-butene gave these same products.