Oxidative coupling of phenols and phenolic ethers. Part 4. Synthesis of dibenz[d,f]azonines and a dibenz[d,f]azacine, via direct coupling

Two series of amides, the N-phenethylphenylacetamides (9) and the bisphenethylamides (11), including diphenolic monophenolic, and non-phenolic types, were treated with a range of one-electron oxidants. With the tetramethoxy-derivative (11e) intramolecular coupling yielded a dibenzazonine (16) in 36% yield. Similar oxidation of the homologue (18) gave a dibenzazecine (19) in 60% yield.