The proof of structure of 9-cyclohexylanthracene and the syntheses of 2',3' and 4'-methyl-2-(α-naphthylmethyl)-benzophenones and 2-(α-naphthylmethyl)-benzophenone

Abstract

In 1947, while working on the aromatic cyclodehydration of ketones to their corresponding substituted anthracenes, Vingiello (1a) attempted to prepare 9-cyclohexylanthracene using this method.

It was evident in the cyclization of o-benzylcyelohexyl-phenone (I) that the hydrol (II) postulated as an intermediate could lose water in two ways, yielding two different compounds 9,10-dihydro-9-cyclohexenylanthracene (IV) and 9-cyclohexyl-anthracene (III). This is shown in Chart I. Since a carbon, hydrogen analysis gives the same result for both compounds it is obvious that some other method of identification is necessary.

It is the purpose of this part of the investigation to attempt to identify the existing structure by ultra-violet absorption analysis, and formation of derivatives and also to attempt to prepare 9-cyclohexylanthracene by an unequivocal method.