Special features of the interaction of pyridine and quinoline derivatives, and related compounds with triphenylphosphine

Abstract

Using pyridine, quinoline, and related compounds as examples, it has been shown that their interaction with triphenylphosphine occurs via different pathways. Reaction of triphenylphosphine with N-vinylisonicotinic acid chloride leads to the mixture of 1,2-bis(triphenylphosphoniumchlorido)ethane and 4-carboxy-2-(triphenylphosphoniumchloridoethyl)pyridine. In the case of α-(N-2-carboxyquinolinylbromido)-β-bromopropionic acid, the reaction with triphenylphosphine proceeds via phosphine attack on the oxygen atom with elimination of quinaldinic acid, and subsequent nucleophilic substitution with the formation of 3-(triphenylphosphoniumbromido) propionic acid bromide.