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Synthesis of 9,10‐Dimethyl‐2,3,6,7‐Anthracenetetra(thioacetate) and Benzenepentathiol; Improved Syntheses of 1,2,4,5‐Benzenetetra(thioacetate) and Benzenehexathiol
ChemistrySelect ( IF 1.9 ) Pub Date : 2016-07-04 , DOI: 10.1002/slct.201600454
Huaiyuan Hu 1 , Mayank Pratap Singh 1 , Garima Singh Baghel 1 , Gregory W. Dye 1 , Deidra L. Gerlach 1 , Thomas P. Vaid 1
Affiliation  

A synthesis is reported for 9,10‐dimethyl‐2,3,6,7‐anthracenetetra(thioacetate), an anthracenetetrathiol derivative that may find use in molecular electronics and conducting metal‐organic frameworks (MOFs). The easily accessible 2,3,6,7‐tetrahydroxy‐9,10‐dimethylanthracene was treated with 2‐(4‐pyridyl)ethanethiol in molten p‐toluenesulfonic acid to yield the tetra(thioether), which was methylated and then deprotected with triethylamine in the presence of acetic anhydride to yield 9,10‐dimethyl‐2,3,6,7‐anthracenetetra(thioacetate), a protected form of the tetrathiol. Separately, the first synthesis of benzenepentathiol and streamlined syntheses of 1,2,4,5‐benzenetetra(thioacetate) and benzenehexathiol are reported.

中文翻译:

9,10-二甲基-2,3,6,7-蒽四(硫代乙酸酯)和苯五硫醇的合成; 1,2,4,5-苯并四(硫代乙酸酯)和苯并六硫醇的合成方法得到改进

据报道合成了9,10-二甲基-2,3,6,7-蒽四(硫代乙酸酯),一种蒽四硫醇衍生物,可用于分子电子学和导电金属有机骨架(MOF)。在熔融的甲苯磺酸中用2-(4-吡啶基)乙硫醇处理易于获得的2,3,6,7-四羟基-9,10-二甲基蒽,得到四(硫醚),将其甲基化,然后用三乙胺在乙酸酐的存在下生成9,10-二甲基-2,3,6,7-蒽四(硫代乙酸酯),四硫醇的保护形式。另外,还报道了苯五硫醇的首次合成以及1,2,4,5-苯四(硫代乙酸酯)和苯六硫醇的流线型合成。
更新日期:2016-07-04
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