Regiospecific, stereospecific ring closure of alkenylperoxyl radicals generated by oxygenation of benzenethiol–triene mixtures

Abstract

Oxygenation of mixtures of benzenethiol and octa-1,3,6-triene (1a) or 5-methylhepta-1,3,6-triene (1b) with free-radical initiation affords, after treatment of the initial products with triphenylphosphine, the 1,2-dioxolans (9a) and (9b), respectively, via mechanisms involving stereospecific and regiospecific ring closure of the alkenylperoxyl radicals (4a) and (4b).