Rearrangements of diphenylamine derivatives. Part V. Rearrangements of 4-substituted N-acyldiphenylamines and related reactions
Abstract
N,4-Dibenzoyldiphenylamine reacts in polyphosphoric acid at 140° to give 4-benzoyldiphenylamine, 4,4′-dibenzoyldiphenylamine, 2-benzoyl-9-phenylacridine, and 2,7-dibenzoyl-9-phenylacridine; the rearrangement of N-benzoyl-4-methyldiphenylamine proceeds analogously. N-Acetyl-4-benzoyldiphenylamine yields only 4-benzoyldiphenylamine and 4-acetyl-4′-benzoyldiphenylamine, and N-butyroyldiphenylamine yields only diphenylamine, 9-propylacridine, and 2-butyroyl-9-propylacridine under similar conditions. C-Alkanoylation is facilitated by increased chain-length in the alkanoyl group, but yields of rearrangement products from the N-alkanoyl compounds are low. 4-Benzoyldiphenylamine, either alone or in the presence of benzoic acid, is converted into 9-phenylacridine by treatment with zinc chloride at 240°.
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