RuO4-mediated oxidation of secondary amines 2. imines as main reaction intermediates

  • Florea C
  • Hîrtopeanu A
  • Stavarache C
  • et al.
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Abstract

Oxidation by RuO4 (generated in situ from RuO2 and NaIO4) of secondary amines such as Bn?NH?CH2R (1; R=H, Me) gave complex reaction mixtures, but mainly amides. In the presence of cyanide, the leading products were ?-aminonitriles. Comparison of the oxidation products of 1 with those from the corresponding imines PhCH=N?CH2R and Bn?N=CH?R showed that formation of the indicated imines is the first main step in the oxidation of 1. A detailed mechanism is proposed.nema

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Florea, C., Hîrtopeanu, A., Stavarache, C., & Petride, H. (2017). RuO4-mediated oxidation of secondary amines 2. imines as main reaction intermediates. Journal of the Serbian Chemical Society, 82(6), 627–640. https://doi.org/10.2298/jsc160914055f

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