Open AccessRuO4-mediated oxidation of secondary amines 2. imines as main reaction intermediates
Author(s) -
Cristina Florea,
Anca Hîrtopeanu,
Cristina Stavarache,
Horia Petride
Publication year - 2017
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc160914055f
Subject(s) - chemistry , cyanide , medicinal chemistry , oxidation process , reaction mechanism , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , chemical engineering , engineering
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 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