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N,N-Dimethyl(1A) and N,N-diethylbenzylamine (1B) underwent RuO4-mediated oxidation by attack at both types of (N-α)C-H bonds (i.e., alkyl and benzyl) to yield the corresponding Nalkyl-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 Nbenzylpiperidine showed that RuO4 does not discriminate axial and equatorial CH bonds in the piperidine ring. The N-α-C carbon-centered radical and the amine cation radical seem not to be involved as precursors of the iminium cations.

RuO4-mediated oxidation of N-benzylated tertiary amines. 2. Regioselectivity for N,N-dimethyl- and N,N-diethylbenzylamine as substrates