HETEROAROMATIC AZO-ACTIVATED NUCLEOPHILIC SUBSTITUTIONS. THE REACTION OF 4-(p-METHOXYPHENYLAZO)PYRIDINIUM METHIODIDE WITH PIPERIDINE IN DIMETHYL SULPHOXIDE

Article abstract of DOI:10.3987/R-1987-02-0313

The azopyridinium-activated phenyl methyl ether, 1, undergoes nucleophilic attack by piperidine in dimethyl sulphoxide predominantly at the aryl carbon centre in a reaction that is base catalyzed and faster than the corresponding reaction of the dinitro-activated analogue, 2, by more than two decades.