Zincke reaction Mechanism

From these various studies, the overall picture that emerged for the Zincke reaction mechanism is outlined in Scheme 8.4.10. When water is excluded, initial... 

The questions raised by Kekule s interpretation of the mechanism of this reaction led to a number of investigations which involved a further study of the oxidation of aromatic phenols and quinones. Thus, for example, Zincke in collaboration with Kuster48 and Rabinowitch 4 undertook a systematic investigation of the action of chlorine (potassium chlorate plus hydrochloric acid) on various derivatives of the three dihydroxybenzenes. The results of these experiments showed that these classes of benzene derivatives split up under conditions to give aliphatic compounds. The intermediate compounds which were formed from tetrahydrobenzene during these transfonnations, were identified as the hexachloro-o-diketone derivative (I) and the pentachloro-m-diketone derivative (II). 

The ANRORC mechanism is operative in a number of named reactions e.g., Zincke-Konig Dimroth and in some instances Chichibabin), that have been known for over 100 years. Seminal work in the 1960s by Henk van der Plas used isotopic labeling to deduce the mechanism of these transformations for a number of systems. Based on van der Plas studies, the acronym ANRORC was coined. ... 

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