Formation of unsymmetrical 1,4-dithiins from fused 1,2,3,4,5-pentathiepins: synthesis, structural, and computational study Научная публикация
| Журнал |
Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416 |
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| Вых. Данные | Год: 2012, Том: 68, Номер: 2, Страницы: 590-597 Страниц : 8 DOI: 10.1016/j.tet.2011.10.113 | ||||
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Реферат:
Pentathiepinopyrroles reacted with methyl propiolate and triphenylphosphine to give regioselectively dithiinopyrroles in agreement with the electron distribution in the proposed reaction intermediate. Thieno[2,3-f][1,2,3,4,5]pentathiepin when treated with methyl propiolate and triphenylphosphine gave a pair of regioisomers where the higher yielding regioisomer contained the same mode of junction as in the case of pentathiepinopyrroles. X-ray crystal structures are provided for the thieno[2,3-b][1,4]dithiine carboxylate isomers. Quantum-chemical calculations B3LYP/6-31G(d) and B3LYP/6-311++G(d,p) have been carried out for better understanding of the reaction mechanisms; the index of synchronism of the Sh addition and the index of a relative difference in bond orders in transition states are in good agreement with the formation of the regioisomers by the reaction of unsymmetrical pentathiepins with alkynes containing one electron-withdrawing group.
Библиографическая ссылка:
Konstantinova L.S.
, Amelichev S.A.
, Belyakov P.A.
, Khakimov D.V.
, Pivina T.S.
, Lyssenko K.A.
, Rakitin O.A.
Formation of unsymmetrical 1,4-dithiins from fused 1,2,3,4,5-pentathiepins: synthesis, structural, and computational study
Tetrahedron. 2012. V.68. N2. P.590-597. DOI: 10.1016/j.tet.2011.10.113 WOS Scopus OpenAlex
Formation of unsymmetrical 1,4-dithiins from fused 1,2,3,4,5-pentathiepins: synthesis, structural, and computational study
Tetrahedron. 2012. V.68. N2. P.590-597. DOI: 10.1016/j.tet.2011.10.113 WOS Scopus OpenAlex
Идентификаторы БД:
| Web of science: | WOS:000299443900023 |
| Scopus: | 2-s2.0-82955163235 |
| OpenAlex: | W2021361317 |