Radical induced 1,3-rearrangement–cyclisations of some unsaturated allylic sulphones

Abstract

1,3-Rearrangement–cyclisation of unsaturated allylic sulphones, typified by the conversion of the pentenyl substituted allyl sulphone (6) into the cyclic sulphone (8), is described. Reaction is considered to occur by a radical chain mechanism involving addition–elimination of ArSO₂˙. The scope of the reaction has been explored, using various methyl substituted substrates of type (13) and other structural variants, and found to be quite general.