Formation of 1,2-dioxolane in the singlet oxygenation of cyclopropane

Article abstract of DOI:10.1016/0040-4039(91)80568-Q

Reaction of 1,1,2,2-tetraanisylcyclopropane (1a) with both thermally and photochemically generated singlet oxygen afforded the corresponding 1,2-dioxolane 2a quantitatively. Singlet oxygenation of two stereoisomeric 1,2-dianisyl-1,2-ditolylcyclopropanes (1b and 1c) gave a mixture of 1,2-dioxolanes 2b and 2c via a non-stereospecific addition in both cases.