N-NITROSO-N-(N-BUTOXYMETHYL)ARYLAMINES

The title compounds were promptly obtained in fair to good yields as d istillable liquids by admiring 1,3,5-triarylhexahydro-1,3,5-triazines (1) with n-butyl nitrite (2) in anhydrous CH2Cl2 and were fully charac terized by H-1 and (13)CNMR, IR, and MS. The pure products were invari ably made up of geometric isomers which did not interconvert rapidly a t room temperature. o-Substituents could cause difficulties in the fre e rotations of the aryl substituent about the C-N bond as well of the alpha-butoxymethyl group. The reaction is believed to occur on the mon omeric imines derived from the thermal equilibration of their trimeric and dimeric precursors. Aliphatic hexahydrotriazines were found to be unreactive under the present conditions.