Abstract
The formation of perhydro-1,3-oxazine derivatives (3) through the cyclization reaction of p -nitrobenzaldehyde with cis - (1) and trans -2-aminomethyl-1-cyclohexanol (2) or with their N-methyl derivatives (1m and 2m) were studied by 1H NMR spectroscopy in CDCl 3. The reactions with 1 and 2 proceeded via open-chain intermediates whereas those with 1m and 2m showed no signs of these intermediates. The cyclization reactions of the N-methyl substituted cyclohexanols (1m and 2m) were much faster than those of the corresponding hydroxymethylcyclohexylamines studied earlier. The cyclization of 1 was kinetically controlled but in much lesser extent than the corresponding reaction with cis -2-hydroxymethyl-1-cyclohexylamine. These results confirmed that the cyclization reactions of p -nitrobenzaldehyde with 2-aminomethyl-1-cyclohexanols and their N -methyl derivatives parallel to those with 2-hydroxymethyl-1-cyclohexylamines and their N -methyl derivatives are not usually diastereospecific.
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