Free radical rearrangement of bicyclo [2.2.2]- and bicyclo[4.2.0]octenones systems

Article abstract of DOI:10.1016/S0040-4020(01)86296-7

Intramolecular cyclization of carbon radicals to carbnyl groups was carried out on bicyclo[2.2.2]-and bicyclo[4.2.0]octenones. An unexpected ring expansion product 19, produed by β-scission of the intermediate alkoxyl radical 22, was observed, the β,γ-situated double bond of the bicyclic ketones appears to have a dampening effect on th carbon radical-ketone cyclization and the allylic cleavage of the alkoxyl radical.