Gabriel Synthesis of Hexakis(aminomethyl)benzene and Its Derivatization,ChemistrySelect

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Gabriel Synthesis of Hexakis(aminomethyl)benzene and Its Derivatization
ChemistrySelect ( IF 1.9 ) Pub Date : 2018-06-11 , DOI: 10.1002/slct.201800985
Junya Masuda ₁ , Seiya Kondo ₁ , Yoshiteru Matsumoto ₁ , Masamichi Yamanaka _{1,

2}

Affiliation

Hexakis(aminomethyl)benzene, which is a key precursor for various hexa‐substituted functional molecules, was synthesized by Gabriel synthesis. Nucleophilic substitution of hexakis(bromomethyl)benzene with potassium phthalimide gave hexakis(phthalimidemethyl)benzene in excellent yield. Hydrazinolysis of the phthalimide moieties of hexakis(phthalimidemethyl)benzene afforded a mixture of hexakis(aminomethyl)benzene and 2,3‐dihydrophthalazine‐1,4‐dione. Pure hexakis(aminomethyl)benzene was isolated as its hexahydrochloride upon treating the mixture with HCl. Hexakis‐amides and hexakis‐tosylamide were prepared from hexahydrochloride of hexakis(aminomethyl)benzene in good to high yields. Alkyl‐substituted hexakis‐amide shows extremely high solubility in non‐polar organic solvents like chloroform and n‐hexane. Density functional theory calculation of the structure of hexakis‐amide show that all substituents were oriented to the same side (aaaaaa conformation) via intramolecular hydrogen bonding.

中文翻译：

六（氨基甲基）苯的加百利合成及其衍生化

六（氨基甲基）苯是各种六取代功能分子的关键前体，是通过Gabriel合成法合成的。用邻苯二甲酰亚胺钾对六（溴甲基）苯进行亲核取代，得到的六（邻苯二甲酰亚胺甲基）苯具有优异的收率。六（邻苯二甲酰亚胺甲基）苯的邻苯二甲酰亚胺部分的水合肼解反应得到了六（氨基甲基）苯和2,3-二氢邻苯二甲腈-1,4-二酮的混合物。用HCl处理该混合物后，分离出纯的六（氨基甲基）苯作为六盐酸盐。由六（氨基甲基）苯的六盐酸盐制备六六酰胺和六甲苯磺酰胺，收率高至高。烷基取代的六-酰胺的节目在如氯仿和非极性有机溶剂中非常高的溶解度Ñ己烷六酰胺结构的密度泛函理论计算表明，所有取代基均通过分子内氢键取向至同一侧（aaaaaa构象）。

更新日期：2018-06-11

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