Mn(III)-based oxidative free-radical cyclizations of γ,γ-bis(allylic) acetoacetates

Article abstract of DOI:10.1016/S0040-4020(01)92231-8

Oxidative free-radical cyclizations of γ,γ-(bis)allylic acetoacetates demonstrate that 1,1-disubstituted double bonds are much more reactive than mono- or chloroalkyl-substituted double bonds. The products isolated suggests that bicyclo[3.2.1]octanes 25, 31, 33 and 36 are formed from boat cyclohexyl radical 42 and tandem cyclization products 30, 37 and 38 are obtained from boat cyclohexyl radical 41.