Abstract :
Aprotic diazotization of anthranilic acid with isoamylnitrite or amylnitrite gave benzenediazonium-2-carboxylate. Subsequent thermal decomposition of this diazonium salt (in situ) in 1,2-dichloroethane as a solvent at 85C and in the presence of 2,5-dienthyl-3,4-diphenylcyclopentadienone as a trapping agent gave 1,4-diethyl-2,3-diphenylnaphthalene in high yield, after loss of carbon monoxide. Also, thermal decomposition of this diazonium salt (in situ) was carried outin 1,1,2-trichloroethane as a solvent at 108C in the presence of 2,5-dimethyl-3,4-diphenylcyclopentadienone (monomer) and after loss of carbon monoxide, 1,4-dimethyl-2,3-diphenylnaphthalene was obtained in excellent yield. These naphthalene derivatives were studies by IR, 1H-NMR, 13C-NMR mass spectra and elemental analysis.
