Formation of unsymmetrical 1,4-dithiins from fused 1,2,3,4,5-pentathiepins: synthesis, structural, and computational study

Formation of unsymmetrical 1,4-dithiins from fused 1,2,3,4,5-pentathiepins: synthesis, structural, and computational study Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2012, Volume: 68, Number: 2, Pages: 590-597 Pages count : 8 DOI: 10.1016/j.tet.2011.10.113

Authors

Konstantinova Lidia S. ¹ , Amelichev Stanislav A. ¹ , Belyakov Pavel A. ¹ , Khakimov Dmitry V. ¹ , Pivina Tatyana S. ¹ , Lyssenko Konstantin A. ² , Rakitin Oleg A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str., 28, 119991 Moscow, Russia

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.

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

Web of science:	WOS:000299443900023
Scopus:	2-s2.0-82955163235
OpenAlex:	W2021361317

DB	Citing
OpenAlex	4
Scopus	4
Web of science	3