Abstract

Bulky 2,6-dibenzhydryl-4-methylaniline, I undergoes diazotization upon treatment with \(\hbox {H}_{2}\hbox {SO}_{4}/\hbox {NaNO}_{2}\), which upon further reaction with KI affords 1-iodo-2,6-dibenzhydryl-4-methylbenzene, 1. Reaction of I with one equivalent of acetylacetone in ethanol under reflux condition affords mono-Schiff base, 4-(2,6-dibenzhydryl-4-methylphenylamino)pent-3-ene-2-one, 2. Similarly, I reacts with half equivalent of 2-hydroxy-5-methylisophthalaldehyde or one-third equivalent of 2,4,6-trihydroxybenzene-1,3,5-tricarbaldehyde in ethanol under reflux condition to afford bis-Schiff base, 2,6-bis(((2,6-dibenzhydryl-4-methylphenyl)imino)methyl)-4-methylphenol, 3 and tris-Schiff base, 2,4,6-tris(((2,6-dibenzhydryl-4-methylphenyl)amino)methylene)cyclohexane-1,3,5-trione, 4, respectively. Further, I upon reaction with triflic acid affords (2,6-dibenzhydryl-4-methylphenyl)ammonium triflate, 5 whereas upon reaction with HBr and HCl affords co-crystals I \(\cdot \)HBr, 6 and I \(\cdot \)HCl, 7. All the new products were isolated in moderate to good yield and characterized by spectroscopic (IR, ESI-mass, NMR, UV-Vis) and microanalytical (CHN) techniques, in addition to a single crystal X-ray diffraction study for 1, 2 and 4-7.

Graphical Abstract

JCSC-D-17-00649 Synopsis A bulky amine was employed to synthesise various compounds containing 2,6-dibenzhydrylphenyl group. These compounds include a bulky iodo-derivative, one mono-, one bis- and one tris-Schiff base, one triflate salt of the bulky amine and two co-crystals of the bulky amine with HBr or HCl.

中文翻译：

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立体阻碍的2,6-二苯甲酰基-4-甲基苯基衍生的配体系统：合成与结构

摘要

笨重2,6- dibenzhydryl -4-甲基苯胺，我经历重氮化在治疗\（\ hbox中{H} _ {2} \ {hbox中SO} _ {4} / \ hbox中的NaNO {} _ {2} \） ，与KI进一步反应后得到1-碘-2，6-二苯甲酰基-4-甲基苯1。使I与一当量的乙酰丙酮在乙醇中在回流条件下反应，得到单席夫碱4-（2，6-二苯甲酰基-4-甲基苯基氨基）戊-3-烯-2-酮2。同样，我在回流条件下与一半当量的2-羟基-5-甲基间苯二甲醛或三分之一当量的2,4,6-三羟基苯-1,3,5-三甲醛在乙醇中反应，得到双席夫碱2 6-双（（（（2,6-dibenzhydryl-4-methylphenyl）imino）methyl）-4-甲基苯酚，3和三-席夫碱，2,4,6-三（（（2,6-二dibenzhydryl -4-甲基苯基）氨基）亚甲基）环己烷-1,3,5-三酮，4，分别。此外，I与三氟甲磺酸反应后得到三氟甲磺酸（2,6-二苯甲酰基-4-甲基苯基）铵，5，而与HBr和HCl反应则得到共结晶I \（\ cdot \） HBr，6和I \（\ cdot HCl，7。所有的新产品在中度至良好的产率分离和表征通过光谱（IR，ESI质谱，NMR，UV-VIS）和微量分析（CHN）技术，除了单晶X射线衍射研究为1，2和4 - 7。

图形概要

JCSC-D-17-00649 概述使用大体积胺来合成各种含有2，6-二苯甲酰基苯基的化合物。这些化合物包括大体积的碘衍生物，一种单，一个双和一个三席夫碱，一种大胺的三氟甲磺酸盐和两种大胺与HBr或HCl的共结晶。