LOW-TEMPERATURE FLOW NMR INVESTIGATION OF THE REACTION OF 2,4,6-TRINITROANISOLE WITH SECONDARY-AMINES

Low-tempcraturc flow NMR has been used to investigate the reaction of 2, 4, 6-trinitroanisole with secondary amines in 50% Me2SO -50% MeOH solvent. It is found that the σ complex on the substitution pathway (i.e., by attack of the amine at Ci) is formed in a very fast reaction and that it is relatively stable under these conditions. The system docs not yield the expected substitution, however. Instead a side reaction involving the solvent methanol occurs yielding the 1, 1-dimethoxy McIsen-heimer complex. © 1979, American Chemical Society. All rights reserved.