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dc.contributor.author | Vedernikov N. | |
dc.contributor.author | Miftakhov R. | |
dc.contributor.author | Borisoglebski S. | |
dc.contributor.author | Caulton K. | |
dc.contributor.author | Solomonov B. | |
dc.date.accessioned | 2018-09-17T20:11:17Z | |
dc.date.available | 2018-09-17T20:11:17Z | |
dc.date.issued | 2002 | |
dc.identifier.issn | 0009-3122 | |
dc.identifier.uri | https://dspace.kpfu.ru/xmlui/handle/net/133155 | |
dc.description.abstract | Condensation of 2-pyridylmethyllithium or (6-methyl-2-pyridyl)methyllithium nucleophiles and pyridine, 2-picoline, or 4-tert-butylpyridine as electrophiles leads to new polydentate N-donor ligands, methyl-, tert-butyl-substituted tripyridinedimethanes, or to tripyridinedimethane itself, in good or high yields. Depending on the reagent ratio, solvent used, and reaction conditions, the corresponding intermediate dipyridinemethanes can be minor by-product or major products of the condensation. In contrast to 2-pyridylmethyllithium, lithiated 2-isopropylpyridine does not react with pyridine electrophiles. Vice versa, nucleophilic substitution at the C(2)-pyridine carbon of 2,2-bis(2-pyridyl)propane with 2-pyridylmethyllithium takes place to produce products of condensation of 2-isopropylpyridine and dipyridylmethyllithium. DFT calculations of the Gibbs free energies of reactions combined with pKa values of the CH-acids involved help to explain the reactivity observed. | |
dc.relation.ispartofseries | Chemistry of Heterocyclic Compounds | |
dc.subject | (6-methyl-2-pyridyl) methyllithium | |
dc.subject | 2,6-lutidine | |
dc.subject | 2-picoline | |
dc.subject | 2-pyridylmethyllithium | |
dc.subject | 4-tert-butylpyridine | |
dc.subject | C-C bond cleavage | |
dc.subject | Condensation | |
dc.subject | DFT calculations | |
dc.subject | Dipyridinemethanes | |
dc.subject | Gibbs free energy of reaction | |
dc.subject | Pyridine | |
dc.subject | tripyridinedimethanes | |
dc.title | Condensation of 2-pyridylmethyllithium nucleophiles and pyridine electrophiles as a convenient synthetic route to polydentate chelating N-donor ligands | |
dc.type | Article | |
dc.relation.ispartofseries-issue | 4 | |
dc.relation.ispartofseries-volume | 38 | |
dc.collection | Публикации сотрудников КФУ | |
dc.relation.startpage | 406 | |
dc.source.id | SCOPUS00093122-2002-38-4-SID0036554655 |