REACTION OF SINGLET OXYGEN WITH METHYLENECYCLOPROPANES: FORMATION OF 4-METHYLENE-1,2-DIOXOLANES

Article abstract of DOI:10.1016/S0040-4039(00)95690-9

Photosensitized oxygenation of adamantylidenecyclopropanes gave either the corresponding 4-methylene-1,2-dioxolane or lactone and cyclic ketone depending on the substituent on the cyclopropane ring.The results are rationalized in terms of initial formation of a perepoxide intermediate followed by that of an allylic cation-type zwitterion or a carbonyl oxide, respectively.