The formation of ozonides by electron transfer induced photo-oxidation of small-ring cycloalkenes

Abstract

Several polymethyl-1,2-diphenylcyclobutenes have been subjected to photo-oxidation in acetonitrile in the presence of 9,10-dicyanoanthracene and it is possible to isolate the corresponding ozonides, in moderate yields (ca. 13%), apparently formed from oxirans produced in a primary step; 1,4-diketones are not generated from the ozonides under the reaction conditions although they are formed as reaction products by what must be an alternative mechanism.