2-Bromo-3-methyl-1,4-naphthoquinone and 2-methyl-1,4-naphthoquinone are highly reactive species known to dimerize in various ways. The product obtained in the dimerization of each compound is primarily dependent upon the solvent used. Ionic liquids represent a new class of solvents having non-molecular (ionic) character. Replacement of a conventional organic solvent with an ionic solvent frequently changes the mechanism of a reaction. In this study, reactions of 2-bromo-3-methyl-1,4-naphthoquinone and 2-methyl-1,4-naphthoquinone in ionic liquids were examined. Dimerization of 2-bromo-3-methyl-1,4-naphthoquinone or 2-methyl-1,4-naphthoquinone with N-methylcyclohexylamine in tetra-n-butylammonium bromide (TBAB), an ionic liquid, under an aerobic atmosphere afforded 5,7,12,14-pentacenetetrone and 1-methylKuQuinone, respectively. The use of TBAB as a solvent improved the yields of the products as compared with previously reported methods. The mechanism of each dimerization was also investigated.

2-溴-3-甲基-1,4-萘醌和2-甲基-1,4-萘醌是高反应性物种，已知其以各种方式二聚。每种化合物二聚得到的产物主要取决于所用溶剂。离子液体代表了具有非分子（离子）特性的新型溶剂。用离子溶剂代替常规有机溶剂经常改变反应机理。在这项研究中，研究了2-溴-3-甲基-1,4-萘醌和2-甲基-1,4-萘醌在离子液体中的反应。2-溴-3-甲基-1,4-萘醌或2-甲基-1,4-萘醌的二聚化用Ñ -methylcyclohexylamine在四Ñ在有氧气氛下，离子液体溴化丁基溴化铵（TBAB）分别得到5,7,12,14-戊烯酮和1-甲基KuQuinone。与先前报道的方法相比，使用TBAB作为溶剂提高了产物的产率。还研究了每个二聚化的机理。