The chemistry of small-ring compounds. Part 51. Electron-transfer-initiated oxidation of some cyclopropylidene compounds

Article abstract of DOI:10.1002/recl.19871061103

Cyclopropylidene compounds of type 1 are found to quench the fluorescence of 9,10-dicyanoanthracene (DCA).Nevertheless photo-oxygenation, in the presence of DCA, leads under no circumstances to dioxetanes but (in ethanol) to a methoxy hydroperoxide 5, as tentatively shown in Scheme 2.This hydroperoxide undergoes acid rearrangement either to a lactone or to a cyclobutanone, depending on the reaction conditions (Scheme 3).