Vicarious Nucleophilic Hydroxylation of aromatic nitro compounds with organic hydroperoxides
作者:Thomas Brose、Felix Holzscheiter、Gunter Mattersteig、Wilhelm Pritzkow、Volkmar Voerckel
DOI:10.1002/prac.19923340609
日期:——
Nitrobenzene, alpha-nitronaphthalene, m-dinitrobenzene, 1,3,5-trinitrobenzene, m-nitrobenzophenone, m-nitrobenzonitrile, methyl m-nitrobenzoate and m-nitro diphenylsulphone can be hydroxylated with cumene or tert-butyl hydroperoxide in dipolar aprotic solvents in the presence of strong bases. The hydroxyl group is introduced preferably in p-position to the nitro group. Attempts to hydroxylate benzophenone, anthraquinone, 2-ethyl anthraquinone, anthraquinone 2-sulphonate, benzonitrile and diphenyl sulphone under the same conditions failed. 1-Nitroanthraquinone delivered 1-hydroxy, 1,2-dihydroxy and 1,4-dihydroxy anthraquinone.