An efficient electrochemical method for the synthesis of N,N,N′,N′-tetraalkyl-4,4′-azodianiline

• Electrochemical synthesis of N,N,N′,N′-tetraalkyl-4,4′-azodianiline.
• Electrochemical oxidation of N,N-dialkyl-p-phenylenediamine.
• Describing an ECE mechanism.
• Constant-current synthesis of N,N,N′,N′-tetraalkyl-4,4′-azodianiline.
• Green chemistry.

Electrochemical synthesis of two N,N,N′,N′-tetraalkyl-4,4′-azodianiline derivatives was carried out via electrochemical oxidation of N,N-dialkyl-p-phenylenediamine in an aqueous solution. The results showed that electrochemically generated p-quinone-diimines in a Michael-type reaction with the starting molecules (N,N-dialkyl-p-phenylenediamine) and via an “electron transfer + dimerization reaction + electron transfer” (ECE) mechanism, were converted to the corresponding N,N,N′,N′-tetraalkyl-4,4′-azodianiline derivatives. In this work, two tetraalkyl-4,4′-azodianiline derivatives with high yields in aqueous solutions, without toxic reagents and solvents at a carbon anode electrode using an environmentally friendly novel method, are provided.

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