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Oxidation of tertiary amines with N‐chloronylon 66 (NCN) was investigated in several organic solvents. NCN was found to oxidize N,N‐dimethylaniline (DMA) at room temperature to give N‐methylaniline with 15–50% yield, depending on the solvents used. Oxidation of N,N‐dimethylbenzylamine (DMBA) gave benzaldehyde with 15–30% yield and a small amount of N‐methylbenzylamine. A mechanism was discussed. For comparison, N‐chlorosuccinimide, a low molecular N‐chloro‐compound, was also used for oxidation of DMA and DMBA.
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Sato et al. (1979) studied this question.
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