RuO4-Mediated oxidation of secondary amines. 1. Are hydroxylamines main intermediates?

Cristina Antoneta Florea, Horia Petride

Abstract


The RuO4-catalyzed oxidation of secondary amines Bn-NH-CH2R (1a-b; R=H, Me) gave mainly amides, but minute amounts of nitrones PhCH=N(O)-CH2R (9a-b) and traces of Bn-N(OH)-CH2R (R=H, 4a) were also detected. In the presence of cyanide, up to 22 reaction products were identified, but mainly α-aminonitriles. Comparison of the oxidation products of 1a-b with those of 4a-b, 9a-b, and Bn-N(O)=CHR (10a-b) showed that 4a-b cannot be main reaction intermediates formed from 1a-b


Keywords


oxidation; secondary amines; ruthenium tetraoxide; hydroxyl¬amines; nitrones.

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DOI: https://doi.org/10.2298/JSC151215029F

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