Synthesis of naphthalene and binaphthyl derivatives via arynes intermediates

Abstract

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