COMPETITION ENTRE SUBSTITUTION NULCEOPHILE ET REDUCTION CHEZ LES BROMO-9 ANTHRACENES DANS L'ACTION DES ANIONS PHENATE ET METHYLATE; APPLICATION A LA MONO-DEUTERIATION SPECIFIQUE EN MESO EN SERIE ANTHRACENIQUE

Article abstract of DOI:10.1016/0040-4020(82)80052-5

Treatment of meso-substituted 9-bromoanthracenes bearing no hydrogen in the α position with potassium phenoxide in DMF gives rise to a competition between nucleophilic substitution and reductive dehalogenation.Derivatives carrying electron attracting groups, 1c (Br), 1e (CN) and 1f (NO2), react essentially by substitution leading to phenolic ethers 2, whereas with non-activated bromides, 1a (H), 1b (C6H5) and 1d (OC6H5), the main reaction is a reduction to anthracenes 3 which should arise from an electron transfer.A reduction of 9-bromoanthracene into anthracene is also observed with sodium methoxide and it is shown, by labelling, that this one must result from a hydride transfer from methoxide.It may be applied to the specific meso-monodeuterization of various anthracenic derivatives.