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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
Author(s) -
Hu Huaiyuan,
Singh Mayank Pratap,
Baghel Garima Singh,
Dye Gregory W.,
Gerlach Deidra L.,
Vaid Thomas P.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600454
Subject(s) - yield (engineering) , ethanethiol , chemistry , triethylamine , thioether , acetic anhydride , derivative (finance) , organic chemistry , materials science , catalysis , economics , financial economics , metallurgy
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.