Radical-induced 1,3-rearrangements of allylic sulfones bearing an alkylthio or arylthio substituent at the α-position
Abstract
1-Methylthio-1-p-tolylsulfonylprop-2-ene 2 underwent 1,3-rearrangement under conditions of radical initiation with migration of the p-tolylsulfonyl group by a process considered to have involved addition–elimination of arylsulfonyl radicals. In contrast, the reaction of 1-p-tolylthio-1-p-tolylsulfonylprop-2-ene 3 under similar conditions gave scrambled products, indicating that arylthio and arylsulfonyl radicals participate with about equal efficiency.