First examples of phase transfer catalysis in electrophilic substitution reactions. Acceleration of the azo coupling reaction

Abstract
Coupling reactions between 4-nitrobenzenediazonium chloride and N-ethylcarbazole or NN-diphenylamine in aqueous media are accelerated by using a two-phase water–dichloromethane system containing sodium 4-dodecylbenzenesulphonate as a transfer catalyst for the diazonium ion.

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