Journal of Organic Chemistry p. 3091 - 3094 (1985)
Update date:2022-08-02
Topics:
Stahly, G. Patrick
The anion of 2,6-di-tert-butylphenol (1) behaves as a carbon nucleophile toward nitroarenes bearing leaving groups ortho or para to the nitro group, affording biphenyls by conventional SNAr processes.However, 1 reacts with m-dinitrobenzene (2), o-nitrobenzonitrile, or m-nitrobenzonitrile to give biphenyls by displacements of nitroarene hydrogen atoms.This oxidative coupling process also occurs between unhindered phenols, even phenol itself, and compound 2.Mechanistic features of the oxidative coupling reaction are discussed.
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