caa a22 4500 475759508 CHVBK 20180406123546.0 cr unu---uuuuu 170329e20000701xx s 000 0 eng 10.1007/BF02495775 doi (NATIONALLICENCE)springer-10.1007/BF02495775 Cyclopenta[ b ]thienyl ligand in organometallic chemistry. Studies of the regioselectivity of the synthesis of new σ-element-substituted cyclopenta[ b ]thiophene derivatives [Elektronische Daten] [D. Kissounko, M. Zabalov, Yu. Oprunenko, D. Lemenovskii] Reactions of 2-ethyl-5-methylcyclopenta[b]thienyllithium (thiopentalenyllithium) (2) with various electrophilic reagents afford σ-element-substituted thiopentalenes. However, the reaction with Ph3SnCl yields only one of two possible isomers,viz, triphenyl(4H-cyclopenta[b] thiophen-4-yl)stannane (4c), whereas the reactions with Me3SiCl, Me3SiCl, or Ph2PCl give both possible isomers,viz., trimethyl(6H-cyclopenta[b]thiophen-6-yl)silane (3a) and trimethyl(4H-cyclopental[b]thiophen-4-yl)silane (4a), trimethyl(6H-cyclopenta[b]thiophen-6-yl)stannane (3b) and trimethyl(4H-cyclopental[b]thiophen-4-yl)stannane (4b), or diphenyl(6H-cyclopenta[b]thiophen-6-yl)phosphine (3d) and diphenyl(4H-cyclopenta[b]thiophen-4-yl)phosphine (4d) in ratios of 1∶2, 1∶2, or 1∶1, respectively. The structure of compound4c was established by X-ray diffraction analysis. The observed regioselectivity of formation of compound4c is attributed to the specific precoordination of the tin atom by the sulfur atom of the thiopentalenyl ligand and to the steric overcrowding of the Sn atom in organotin electrophiles. Kluwer Academic/Plenum Publishers, 2000 thiopentalenyl ligand nationallicence regioselective substitution nationallicence specific precoordination nationallicence Kissounko D. Department of Chemistry, M. V. Lomonosov Moscow State University, Vorob'evy Gory, 119899, Moscow, Russian Federation aut Zabalov M. Department of Chemistry, M. V. Lomonosov Moscow State University, Vorob'evy Gory, 119899, Moscow, Russian Federation aut Oprunenko Yu Department of Chemistry, M. V. Lomonosov Moscow State University, Vorob'evy Gory, 119899, Moscow, Russian Federation aut Lemenovskii D. Department of Chemistry, M. V. Lomonosov Moscow State University, Vorob'evy Gory, 119899, Moscow, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/7(2000-07-01), 1282-1286 1066-5285 49:7<1282 2000 49 11172 https://doi.org/10.1007/BF02495775 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02495775 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Kissounko D. Department of Chemistry, M. V. Lomonosov Moscow State University, Vorob'evy Gory, 119899, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Zabalov M. Department of Chemistry, M. V. Lomonosov Moscow State University, Vorob'evy Gory, 119899, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Oprunenko Yu Department of Chemistry, M. V. Lomonosov Moscow State University, Vorob'evy Gory, 119899, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Lemenovskii D. Department of Chemistry, M. V. Lomonosov Moscow State University, Vorob'evy Gory, 119899, Moscow, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/7(2000-07-01), 1282-1286 1066-5285 49:7<1282 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer