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 |
|