Radical rearrangements of α-iodoalkyl phenyl sulfones involving 1,5 hydrogen atom transfer reactions

α-Iodoalkyl phenyl sulfones undergo radical rearrangement to 5-iodo-1-phenylsulfonyl derivatives when heated with benzoyl peroxide or when irradiated with a sunlamp in the presence of hexabutylditin. Products of these rearrangements, upon treatment with bases, can be easily and stereoselectively converted into trans phenylsulfonyl derivatives of cyclopentane.