Biphenylenes. Part XXVIII. Synthesis of some benzo[b]-, naphtho-[2,3-b]-, and anthra[2,3-b]-derivatives of biphenylene

Abstract

The Friedel–Crafts acylation of biphenylene with the anhydrides of succinic, phthalic, and naphthalene-2,3-dicarb-oxylic acids has been studied. The resulting acylbiphenylenes were then converted into benzo[b]-, naphtho-[2,3-b]-, and anthra[2,3-b]-biphenylene para-quinones [(1), (10), and (14)] and thence into other compounds including the anthracene and tetracene hydrocarbons [(11) and (13); R = H]. Acylation of biphenylene with maleic anhydride followed by attempted ring closure gave a blue Pechmann dye (8).