Scholl reaction, investigations

Scholl and his colleagues have investigated this reaction, which is accordingly known as the Scholl reaction.270,2710... 

Rempala P, Kroulik J, King BT (2006) Investigation of the mechanism of the intramolecular Scholl reaction of contiguous phenylbenzenes. J Org Chem 71 5067-5081. doi 10.1021/... 

Neither the synthetic scope nor mechanism was significantly investigated until 1935, when Baddeley and co-workers provided new insights into the Scholl reaction. Their work provided the first mechanistic interpretation, suggesting that the homocoupling reaction of naphthalene proceeds via an arenium cation intermediate. Based on experiments in... 

The ability of Br0nsted acids to increase the oxidizing power of benzoquinone derivatives was further investigated by Rathore in the context of the Scholl reaction [246], Arene substrates with oxidation potentials as high as -1-1.7 V vs. SCE were readily oxidized by dichlorodicyano-p-benzoquinone (E — -1-0.60 V vs. SCE) in the presence of methane sulfonic acid (Fig. 38). However, no reaction was observed in the absence of acid. 

The possible reaction pathways in the DDQ-mediated Scholl reaction were also well investigated by Rathore, and the authors propose that the reaction likely proceeds through a radical cation intermediate (Path A) (Scheme 8.41). They also referred to the existence of Path B which involves the formation of an arenium ion intermediate. 

The cleavage of tertiary amines by cyanogen bromide (equation 51) was first observed by von Braun and Scholl and Nor in 1900. The reaction was investigated extensively by von Braun it has recently been reviewed by Hageman . ... 

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