- MISE EN EVIDENCE DE LA DEPROTONATION DU COMPLEXE IPSO-ARENIUM OBTENU EN PHENYLATION CATIONIQUE DU DIMETHYL-1,4 NAPHTALENE
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The phenyl cations obtained from the thermolysis of benzenediazonium tetrafluoroborate react with 1,4-dimethylnaphthalene in DMSO to give 1-methyl 4-methylene 1-phenyl 1,4-dihydronaphthalene as well as the phenylation products at positions 2,5 and 6.The formation of the former provides direct evidence for the attack of C6H5+ ipso to the methyl group.Either in pure 1,4-dimethylnaphthalene or in acetonitrile solution, the deprotonation of the ipso-arenium ions has not been observed and the main reaction was the 1-2 migration of the phenyl group.The reactivity of the ipso position in regard to attack by phenyl cations and the reactivity of the 2 position are very similar. 1-methyl 4-phenyl naphthalene has not been detected by G L C so that demethylphenylation of 1,4-dimethylnaphthalene must be negligible.
- Court, J.,Ioakimoglou, H.,Lambeaux, C.,Bonnier, J. M.
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p. 5601 - 5606
(2007/10/02)
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