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

Author:

Florea Cristina1,Hîrtopeanu Anca1,Stavarache Cristina1,Petride Horia1

Affiliation:

1. Romanian Academy, “Costin D. Nenitzescu” Center of Organic Chemistry, Bucharest, Romania

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.

Publisher

National Library of Serbia

Subject

General Chemistry

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