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• W2098597429 abstract "Imidoyl radicals 5, obtained from imines 1 by hydrogen abstraction with di-iso-propyl peroxydicarbonate (DPDC), give dibenzoxazepines through 7-membered ring closure. A competitive 6-membered cyclisation leads to intermediate spirocyclohexadienyl radicals that rearrange to aryloxy radicals; this process entails a novel 1,5-aryl radical translocation from an oxygen to a carbon atom and leads to benzophenones, benzoxazoles, and biphenyls. The possibility that the oxazepines arise from rearrangement of the 6-membered-ring-closure intermediates is discussed. With imine 1e, the formation of 5e occurs to a minor extent owing to a side-reaction of the iso-propoxycarbonyloxy radicals, which give rise to an intermolecular aromatic ipso-substitution on the benzenic ring linked to the two oxygen atoms. The 1,5-aryl migration can also be observed with imidoyl radicals generated by radical addition to 2-phenoxyisocyanobenzene. In contrast, the reactions of imines 2 with DPDC do not afford imidoyl radicals, as abstraction of the iminic hydrogen is slower than oxidation of the methyl group: this process entails the formation of carbamoyl radicals, which cyclise onto the carbon-nitrogen double bond, furnishing quinoxalinone derivatives, or loose carbon monoxide to yield benzimidazoles through ring closure of aminyl radicals. A novel cyclisation of a nitrogen-centred radical onto a formamido group could account for the formation of a benzimidazolinone derivative." @default.
• W2098597429 created "2016-06-24" @default.
• W2098597429 creator A5000313918 @default.
• W2098597429 creator A5001066042 @default.
• W2098597429 creator A5060898366 @default.
• W2098597429 date "1995-10-01" @default.
• W2098597429 modified "2023-10-12" @default.
• W2098597429 title "Peroxydicarbonate-mediated oxidation of N-(ortho-aryloxyphenyl) and N-(ortho-arylaminophenyl)aldimines" @default.
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• W2098597429 doi "https://doi.org/10.1016/0040-4020(95)00769-5" @default.
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