The synthesis and characterization of low-valent organoselenium and tellurium derivatives of hexabromododecahydrotriphenylene has been attempted. The reaction of hexabromododecahydrotriphenylene with in situ generated disodium dichalcogenides (Na2E2; E = Se, Te) afforded insoluble chalcododecahydrotriphenylene derivatives, 20, 21 respectively. Attempted aromatization of 20 and 21 using DDQ (2, 3-dichloro-5, 6-dicyano-1,4-benzoquinone) as an oxidizing agent afforded the co-crystals. The hexaselenophenyl derivative, 22 and the hexaselenocyanate derivative 23 were synthesized by the reaction of in situ generated sodium arylselenolate/potassium selenocyanate with hexabromododecahydrotriphenylene, respectively. The compounds were characterized by common spectroscopic tools and a few by single crystal x-ray crystallographic studies.
Volume 133, 2021
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