The chemistry of ortho-benzoquinones. Part VI. The reaction of primary aromatic amines with alkyl substituted 1,2-benzoquinones: the displacement of alkyl groups in the 4- and 5-positions

Abstract

The reaction of primary aromatic amines with alkyl substituted 1,2-benzoquinones has been investigated. An alkyl Substituent in the 3-position has no effect on the course of the reaction which proceeds as with 1,2-benzoquinone itself (see Part IV),² but primary alkyl groups in the 4(5)-position are displaced by an arylamino-group. If there are methyl groups in both the 4- and the 5-positions only one is displaced. The methyl group in 4-methyl-1,2-naphthoquinone is likewise displaced. With ortho-phenylenediamine no alkyl displacement occurs but alkyl phenazines are formed. The mechanism of the displacement has been elucidated.