RuO4-Mediated oxidation of secondary amines 2. Imines as main reaction intermediates

Cristina Antoneta Florea, Anca Hîrtopeanu, Cristina Stavarache, Horia Petride

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.


Keywords


oxidation; secondary amines; ruthenium tetraoxide; imines; α aminonitriles

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DOI: http://dx.doi.org/10.2298/JSC160914055F

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