RuO4-Mediated oxidation of secondary amines 2. Imines as main reaction intermediates
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Abstract
Oxidation by RuO4 (generated in situ from RuO2 and NaIO4) of secondary amines like Bn-NH-CH2R (1; R=H, Me) gave complex reaction mixtures, but mainly amides. In the presence of cyanide, the leading products were α-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.
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