Reaction of 9-α-chloronaphthylmethylanthracene and its homologues with nucleophiles under solvolytic conditions. Effect of the increase of bulk at C-α on the reaction site
作者:Masato Takagi、Masatomo Nojima、Shigekazu Kusabayashi
DOI:10.1039/p19810002637
日期:——
The reaction of 9-α-chloronaphthylmethylanthracene and its homologues with (a) sodium ethoxide in ethanol, (b) ethanol in the presence of triethylamine, (c) sodium borohydride in aqueous diglyme, and (d) sodium azide in aqueous NN-dimethylformamide has given a mixture of substituted anthracenes and 9,10-dihydroanthracenes. The yield of the latter increases as the aryl group at C-α becomes larger. The
9-α-氯萘甲基甲基蒽及其同系物与(a)乙醇钠在乙醇中,(b)在三乙胺存在下的乙醇,(c)在二甘醇二甲醚水溶液中的硼氢化钠和(d)在NN-二甲基甲酰胺水溶液中的叠氮化钠的反应给出了取代的蒽和9,10-二氢蒽的混合物。随着C-α处的芳基变大,后者的产率增加。在C-10处的氯化物的苯环导致在该位置的反应被延迟。研究了蒽和9,10-二氢蒽之间的相对热力学稳定性。