In the azo coupling of aniline with benzenediazonium cation, I thought of two possible products 1 and 2 that could be formed. However, I can't work out which will be preferred. What would be the major product and why?
Answer
This is a really interesting question and the answer is that the reaction of benzenediazonium chloride with aniline is a bit different to most of the reactions of benzenediazonium salts in that the initial product is compound 1, diazoaminobenzene. It is possible to run the reaction to isolate diazoaminobenzene prep here.
These diazoaminobenzene compounds are unstable with respect to reversion to a diazonium salt + nucleophile, and so many references suggest that compound 2, 4-aminoazobenzene, is directly produced. The procedure for the transformation of diazoaminobenzene 1 to 4-aminoazobenzene 2 is by heating to 50 °C with aniline (prep here).
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