Synthesis of naphthalene and binaphthyl derivatives via arynes intermediates

376-378Benzyne from anthranilic acid has been reacted with 2,5-di-n-propyl-3,4 diphenylcyclopentadienone (n-propylcyclone) in boiling 1,2-dichloroethane to get 1,4-di-n-propyl-2 ,3-diphen-ylnaphthalene in quantitative yield. Bis-benzyne from aprotic diazotization of 3,3'-dicarboxyl-4,4'-diaminobiphenyl is also reacted with this cyclone leading to the formation of a novel polyaromatic adduct 1,1',4,4'-tetra-n-propyl-2,2' ,3,3'-tetraphenyl-6,6'-binaphthyl 6 in a good yield. The above polycyclic aromatic hydrocarbons (PAH,s) have been characterized by high field 1H-NMR, 13C-NMR, IR, mass spectra and elemental analysis. These compounds can be used as analytical samples for the studies of their possible presence in combustion pollutants

Reaction of indanocyclone with 3,4,3',4'-tetradehydrobiphenyl(bisbenzyne)

465-469Diphenyl-4,4'- bis-diazonium-3,3'-dicarboxylate has been prepared from diazotization reaction of 3,3'-dicarboxy-4,4'diaminobiphenyl 4 with isoamylnitrite under aprotic conditions. Thermal decomposition in situ of this diazonium salt in 1,1,2- trichloroethane as a solvent yields 3,4,3',4'-tetradehydrobiphenyl 5 as a reactive intermediate. This reactive intermediate has been trapped with indanocyclone via a [4+2] Diels-Alder cycloaddition reaction. Three isomeric products are formed after loss of carbon monoxide which have been isolated by praparitive TLC. Although these novel polycyclic aromatic hydrocarbons (PAH·s) have similar (IR,1H NMR, mass) spectra and elemental analysis, but they have different Rf values. Three different structures have been proposed for these novel compounds