Synthesis, structure, and one-electron redox reactions of 4,7-disubstituted benzotrichalcogenoles containing sulfur and/or selenium atoms

Stable 4,7-disubstituted benzotrichalcogenoles containing sulfur and/or selenium atoms in the five-membered ring were systematically and selectively prepared in good yields by reaction of the corresponding benzodichalcogenastannoles, a synthetic equivalent of benzenedichalcogenols, with an S 1 or Se...

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Published in:Journal of organometallic chemistry 2000-10, Vol.611 (1), p.136-145
Main Authors: Ogawa, Satoshi, Ohmiya, Tadahito, Kikuchi, Takamasa, Kawaguchi, Atsuko, Saito, Satoshi, Sai, Akihiko, Ohyama, Naomi, Kawai, Yasushi, Niizuma, Shigeya, Nakajo, Shiduko, Kimura, Takeshi, Sato, Ryu
Format: Article
Language:English
Subjects:
Electron transfer
Radical ions
Redox reactions
Selenium heterocycles
Sulfur heterocycles
Voltammetry
X-ray crystal structures
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Summary:Stable 4,7-disubstituted benzotrichalcogenoles containing sulfur and/or selenium atoms in the five-membered ring were systematically and selectively prepared in good yields by reaction of the corresponding benzodichalcogenastannoles, a synthetic equivalent of benzenedichalcogenols, with an S 1 or Se 1 source. Characterization of these new trichalcogenole frameworks was performed by multi-nuclear NMR studies and X-ray crystallographic analyses. The cyclic voltammograms of the trichalcogenoles showed well-defined reversible electrochemical redox couples with low oxidation potential. Novel radical ions were isolated in quantitative yields in the one-electron oxidation of the trichalcogenoles with one equivalent of NOPF 6 as a one-electron oxidant. The structures of the radical cation salts were analyzed by 31P-NMR and EPR spectroscopies, and elemental analyses. The salts underwent one-electron reduction on treatment with one equivalent of samarium(II) iodide to give the neutral starting trichalcogenoles quantitatively.
ISSN:0022-328X
1872-8561
DOI:10.1016/S0022-328X(00)00328-4