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 CBrCl3 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 (CH4, CH3OH, CH3COOCH3, ROCOCH3, CH3COOCH2COCH3), 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.

(1998). Molecule-Induced Homolysis versus "Concerted Oxenoid Oxygen Insertion" in the Oxidation of Organic Compounds by Dimethyldioxirane [journal article - articolo]. In JOURNAL OF ORGANIC CHEMISTRY. Retrieved from https://hdl.handle.net/10446/232890

Molecule-Induced Homolysis versus "Concerted Oxenoid Oxygen Insertion" in the Oxidation of Organic Compounds by Dimethyldioxirane

Fontana, Francesca;
1998-01-01

Abstract

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 CBrCl3 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 (CH4, CH3OH, CH3COOCH3, ROCOCH3, CH3COOCH2COCH3), 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.
articolo
Bravo, Anna; Fontana, Francesca; Fronza, Giovanni; Minisci, Francesco; Zhao, Lihua
(1998). Molecule-Induced Homolysis versus "Concerted Oxenoid Oxygen Insertion" in the Oxidation of Organic Compounds by Dimethyldioxirane [journal article - articolo]. In JOURNAL OF ORGANIC CHEMISTRY. Retrieved from https://hdl.handle.net/10446/232890
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