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4083382 
Journal Article 
RuO4-mediated oxidation of N-benzylated tertiary amines. 2. Regioselectivity for N,N-dimethylbenzylamine and N,N-diethylbenzylamine as substrates 
Petride, H; Costan, O; Draghici, C; Florea, C; Petride, A 
2005 
18-32 
WOS:000238145700003 
N, N-Dimethyl-(1A) and N, N-diethylbenzylamine (1B) underwent RuO4-mediated oxidation by attack at both types of (N-alpha) C-H bonds (i.e., alkyl and benzyl) to yield the corresponding N-alkyl-N- benzylamides [and N-methyl-(8A) or N-ethylbenzylamine (8B), resp.] and benzaldehyde (and N, N-dialkylbenzamides), respectively. Oxidation of 8A-B occurred also, as well as their reaction with formaldehyde or acetaldehyde, respectively, equally formed during the oxidation of 1A-B or 8A-B. Initial formation of the iminium cations from 1A-B was proved by their capture as nitriles. The statistically corrected alkyl/benzyl regioselectivity of the oxidation reaction was 4.1 for 1A and 2.1 for 1B. Comparison with the results obtained on N-benzylpiperidine showed that RuO4 does not discriminate axial and equatorial CH bonds in the piperidine ring. The N-alpha-C. carbon-centered radical and the amine cation radical seem not to be involved as precursors of the iminium cations. 
oxidation; ruthenium tetraoxide; tertiary amines; iminium cations; regioselectivity