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

Cristina Florea | Zendy; Anca Hîrtopeanu | Zendy; Cristina Stavarache | Zendy; Horia Petride | Zendy

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RuO4-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

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