Evidence for a molecule-induced homolysis of dimethyldioxirane by several classes of organic compounds (alkanes, alkenes, ethers, alcohols, aldehydes, iododerivatives) is reported. Carbon-centered radicals, arising from alkanes, ethers, and aldehydes, are trapped by CBrCl 3 or protonated quinolines. The dramatic influence of oxygen in these reactions, as well as the formation of products of induced homolysis of the dioxirane by carbon-centered radicals (CH 4, CH 3 OH, CH 3 COOCH 3, ROCOCH 3, CH 3 COOCH 2 COCH 3 ), strongly supports a radical mechanism. With alkenes and iodo derivatives the induced homolysis would lead to diradical intermediates, whose very fast fragmentation would prevent detection, but circumstantial evidence supports a radical mechanism.
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Bravo et al. (1998) studied this question.