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Abstract
RuO4-mediated oxidation of N-benzylated tertiary amines. 2. Regioselectivity for N,N-dimethyl- and N,N-diethylbenzylamine as substrates
Highlights
In a previous paper[1] we studied the RuO4-mediated oxidation[2] of some N-benzylated cycloalkylamines and found that the attack occurs at both types of N-α-methylene positions,[3] i.e., endocyclic and exocyclic
Oxidation of 8A was repeated in identical conditions as those of entry 6, but some formic acid or formaldehyde was added from the beginning of the reaction
We discovered previously[12] that 1B undergoes oxidation to 8B and 11 in bona fide HAT or ET conditions with regioselectivities of 0.7 and 0.4, respectively
Summary
In a previous paper[1] we studied the RuO4-mediated oxidation[2] of some N-benzylated cycloalkylamines and found that the attack occurs at both types of N-α-methylene positions,[3] i.e., endocyclic and exocyclic (benzylic). In the six-membered cycloalkylamines the endocyclic hydrogens are of two types (i.e., axial and equatorial) and this could influence, almost in principle, the regioselectivity No such stereoelectronic constraints exist in the similar acyclic derivatives. Two types of iminium cation might result in the first step, that is 2A-B (alkyl attack) and 3A-B (benzyl attack) These species are trapped by water and the resulting hemiaminals (4A-B and 5A-B, resp.) could undergo oxidation to the corresponding amides (6A-B and 7A-B, resp.), and cleavage to amine+aldehyde equimolecular mixtures. As will be shown in the following, this was not the case especially because the secondary amines 8A-B underwent oxidation and other reactions by themselves
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