Open AccessRuO4-mediated oxidation of secondary amines: Part 1. Are hydroxylamines main intermediates?
Author(s) -
Cristina Florea,
Horia Petride
Publication year - 2016
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/jsc151215029f
Subject(s) - cyanide , chemistry , medicinal chemistry , stereochemistry , organic chemistry
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