N- Vs. C- Tricyanovinylation of Ring-Substituted Dimethylanilines. The Spectral Properties of the Products.

Methods for changing the selectivity in the N- vs. C- tricyanovinylation are discussed. In acetonitrile, 2,3-, 2,4-, 3,4- and 3, 5-dimethylanilines are N-tricyanovinylated, 2,6-dimethyl- and 2, 6-diethylanilines are p-tricyanovinylated, and 2,5-dimethyl- and 2-ethylaniline give mixtures of N- and p-tricyanovinyl derivatives. The UV, IR, NMR and mass spectra of the products are discussed in relation to the position of the tricyanovinyl group and to electronic and steric effects.