Diels–Alder reactions of 9,10-anthraquinodimethane and 9-methyleneanthrone

Abstract

The addition reactions of 9,10-anthraquinodimethane with maleic anhydride, dimethyl acetylenedicarboxylate, p-benzoquinone, and 1,4-naphthoquinone have been studied. Syntheses of benzo[a]pyrene, dibenzo[j,xyz]-heptaphene and some substituted and reduced derivatives of these hydrocarbons are reported, and the preparation of 1,4:11,14-dibenzo[h,rst]pentaphenediquinone. The reaction of 10-hydroxy-10-methylanthrone with dimethyl acetylenedicarboxylate and with diethyl azodicarboxylate has been investigated; the latter gives the novel 7H-di-benzo[de,h]phthalazine system.