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Condensation of 2-pyridylmethyllithium nucleophiles and pyridine electrophiles as a convenient synthetic route to polydentate chelating N-donor ligands

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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 2018-09-17T21:38:39Z
dc.date.available 2018-09-17T21:38:39Z
dc.date.issued 2002
dc.identifier.issn 0132-6244
dc.identifier.uri https://dspace.kpfu.ru/xmlui/handle/net/135254
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-butylsubstituted tripyridinedimethanes or to tripyridinedimethane itself, in good or high yields. Depending on the reagent ratio, solvent used and reaction condition 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 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 reactions Gibbs free energies combined with pKa values of the CH-acids involved help to explain the reactivity observed.
dc.relation.ispartofseries Khimiya Geterotsiklicheskikh Soedinenii
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 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.collection Публикации сотрудников КФУ
dc.relation.startpage 471
dc.source.id SCOPUS01326244-2002-4-SID0036355012


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  • Публикации сотрудников КФУ Scopus [24551]
    Коллекция содержит публикации сотрудников Казанского федерального (до 2010 года Казанского государственного) университета, проиндексированные в БД Scopus, начиная с 1970г.

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