Friedel–Crafts acylations of aromatic hydrocarbons. Part XIV. Monoacetylation and monobenzoylation of 2,7-dimethylnaphthalene

Abstract

The Friedel–Crafts acetylation or benzoylation of 2,7-dimethylnaphthalene gives mixtures of three isomers, the 1-isomer usually predominating. In acetylations in nitro-solvents equal amounts of the 1- and the 3-(β) isomers are formed. Competitive acetylation experiments in chloroform solution give the following positional reactivities of naphthalene and derivatives: 1- 1·00, 2- 0·31, 2,7-dimethyl-1- 39, 3,6-dimethyl-2- 6·0, and 3,6-dimethyl-1- 3·5; the values for the corresponding benzoylations are 1·00, 0·40, 230, 9·7, and 7·5, respectively.