Effects of substituents on the rates of addition of 2-phenylpropionitrile carbanion to nitroarenes

Abstract

Dedicated to Professor Henk van der Plas on the occasion of his 80th Anniversary AbstractThe effects of substituents located ortho-and meta-to the nitro group in nitroarenes on the rates of addition of 2-phenylpropionitrile carbanion at the para-position were determined using oxidative nucleophilic substitution of hydrogen as the model process via competitive experiments. It was shown that the observed overall effects result from the superposition of primary and secondary electronic and steric effects.