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N‐ Vs. C‐ Tricyanovinylation of Ring‐Substituted Dimethylanilines. The Spectral Properties of the Products.
Author(s) -
Rappoport Z.,
Shohamy Esther
Publication year - 1968
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.196800110
Subject(s) - chemistry , steric effects , acetonitrile , ring (chemistry) , selectivity , electronic effect , mass spectrum , medicinal chemistry , stereochemistry , organic chemistry , mass spectrometry , catalysis , chromatography
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.