Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 27th March 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.

Issue 5, 1997
Previous Article Next Article

Some reactions of ammonia and primary amines with propanal,2-chloroethanal, 2,2-dichloroethanal and 2,2,2-trichloroethanal inacetonitrile


The reaction of ammonia with propanal in acetonitrile produces the hexahydrotriazine, 1, in good yield. The corresponding reaction of chloroethanal yields the cyclic trimer 16 but only in poor yield. Increasing chloro-substitution in the aldehyde stabilises the initially formed carbinolamines and disfavours trimerisation. Imines formed by reaction of primary amines with the aldehydes are relatively stable. Those formed from aliphatic amines may undergo slow dimerisation by C–C bond formation and this may be accompanied by loss of amine to yield products containing a conjugated double-bond system.Kinetic and equilibrium data are reported for both the forward and reverse reactions involving interconversion of propanal and ammonia with 1 in acetonitrile–water mixtures. The results indicate that dehydration of the carbinolamine is rate determining.

Back to tab navigation

Article type: Paper
DOI: 10.1039/A607869I
Citation: J. Chem. Soc., Perkin Trans. 2, 1997,0, 909-916

  •   Request permissions

    Some reactions of ammonia and primary amines with propanal, 2-chloroethanal, 2,2-dichloroethanal and 2,2,2-trichloroethanal in acetonitrile

    M. R. Crampton, S. D. Lord and R. Millar, J. Chem. Soc., Perkin Trans. 2, 1997, 0, 909
    DOI: 10.1039/A607869I

Search articles by author