synthesis of some substituted naphthalenes via benzyne and their 13c-nmr and 'h-nmr studies
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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 85oc and in the presence of 2,5-diethyl-3,4-diphenylcyclopentadienonaes 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 out in 1,1 ,2-trichloroethane as a solvent at 108oc 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 studied by ir, 'h-nmr, 13c-nmr mass spectra and elemental analysis
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Journal title:
journal of sciences islamic republic of iranجلد ۴، شماره ۲، صفحات ۰-۰
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