Abstract
Abstract The title compounds were promptly obtained in fair to good yields as distillable liquids by admixing 1,3,5-triarylhexahydro-1,3,5-triazines (1) with n-butyl nitrite (2) in anhydrous CH2Cl2 and were fully characterized by 1H and 13C NMR, IR, and MS. The pure products were invariably made up of geometric isomers which did not interconvert rapidly at room temperature. o-Substituents could cause difficulties in the free rotations of the aryl substituent about the C–N bond as well of the α-butoxymethyl group. The reaction is believed to occur on the monomeric imines derived from the thermal equilibration of their trimeric and dimeric precursors. Aliphatic hexahydrotriazines were found to be unreactive under the present conditions.
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