Preparation of some Polyaryl-benzenes and -napthalenes

Abstract

Attempts have been made to condense several aromatic α-diketones with diethyl ketone and dibenzyl ketone. 1,1?-Binaphthoyl gave only di-1-naphthylglycolic acid, but 1- naphthyl phenyl diketone gave mixtures of the products of condensation and benzilic acid rearrangement reactions. The condensation product with dibenzyl ketone reacted normally in Diels-Alder reactions with maleic anhydride, benzyne, and bicycloheptadiene. 2-Methylbenzil condensed readily with dibenzyl and diethyl ketones, and the substituted cyclopentadienone resulting from condensation with dibenzyl ketone underwent a Diels-Alder reaction with bicycloheptadiene.