SOME REACTIONS OF AMMONIA AND PRIMARY AMINES WITH PROPANOL, 2-CHLOROETHANOL, 2,2-DICHLOROETHANOL AND 2,2,2-TRICHLOROETHANOL IN ACETONITRILE

The reaction of ammonia with propanal in acetonitrile produces the hex ahydrotriazine, 1, in good yield, The corresponding reaction of chloro ethanal yields the cyclic trimer 16 but only in poor yield, Increasing chloro-substitution in the aldehyde stabilises the initially formed c arbinolamines and disfavours trimerisation. Imines formed by reaction of primary amines with the aldehydes are relatively stable, Those form ed from aliphatic amines may undergo slow dimerisation by C-C bond for mation and this may be accompanied by loss of amine to yield products containing a conjugated double-bond system, Kinetic and equilibrium da ta are reported for both the forward and reverse reactions involving i nterconversion of propanal and ammonia with 1 in acetonitrile-water mi xtures, The results indicate that dehydration of the carbinolamine is rate determining.