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- W2012558702 abstract "In contrast to the high stability of N-alkyl-N-cyclopropylamine derivatives, N-cyclopropyl-N-phenylamine (1a) has been found to slowly convert into the hitherto unknown product N-(1,2-dioxolan-3-yl)-N-phenylamine (1f) at room temperature under aerobic conditions. The rate of this conversion was found to be significantly increased by the presence of a catalytic amount of the single-electron oxidizing agent tris(1,10-phenanthroline)FeIII hexafluorophosphate or of the hydrogen-abstracting agents benzoyl peroxide or tert-butyl peroxide/UV light. Based on the regio- and stereochemical outcomes of aerobic ring-opening reactions of some specifically ring-methylated derivatives of 1a, namely N-(1-methylcyclopropyl)-N-phenylamine (2a), N-(trans-2-methylcyclopropyl)-N-phenylamine (3a), and N-(cis-2-methylcyclopropyl)-N-phenylamine (4a), as well as other experimental evidence, an autocatalytic mechanism analogous to that of the oxygenation of vinylcyclopropanes is proposed for the formation of the 1,2-dioxolane product. The oxidative radical ring opening and related chemistry of these novel derivatives could be valuable in mechanistic studies of heteroatom-oxidizing enzymes." @default.
- W2012558702 created "2016-06-24" @default.
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- W2012558702 date "2001-10-01" @default.
- W2012558702 modified "2023-10-07" @default.
- W2012558702 title "Autocatalytic Radical Ring Opening ofN-Cyclopropyl-N-phenylamines Under Aerobic Conditions − Exclusive Formation of the Unknown Oxygen Adducts,N-(1,2-Dioxolan-3-yl)-N-phenylamines" @default.
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- W2012558702 doi "https://doi.org/10.1002/1099-0690(200110)2001:20<3811::aid-ejoc3811>3.0.co;2-6" @default.
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