Abstract
In connection with a systematic investigation of the colour reaction of phenols to form quinoneimine dyes the reaction of phenol with 4-dimethylaminoantipyrine and an oxidizing agent has been studied. Though it has been found that the resulting coloured reaction product is identical with that of the reaction of phenol with 4-aminoantipyrine and an oxidizing agent (Emerson reaction), a different mechanism is operative. The reaction of phenol with 4-dimethylaminoantipyrine seems to proceed through oxidative degradation to 4-aminoantipyrine which reacts with phenol according to the Emerson reaction. In the literature this has been explained as occuring with intermediate formation of a quinoneimine, for which the presence of ammonium ions in the reaction mixture is necessary. In this communication the role of the ammonium ions is explained as inhibition of the decomposition of 4-dimethylaminoantipyrine to form imino-bis-phenazone. Phenol can also react with aminophenazone and an oxidizing agent in the absence of ammonium ions.
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