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Features of the Diels-Alder reaction between 9,10-diphenylanthracene and 4-phenyl-1,2,4-triazoline-3,5-dione

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dc.contributor.author Kiselev V.
dc.contributor.author Kornilov D.
dc.contributor.author Kashaeva E.
dc.contributor.author Potapova L.
dc.contributor.author Krivolapov D.
dc.contributor.author Litvinov I.
dc.contributor.author Konovalov A.
dc.date.accessioned 2018-09-18T20:31:32Z
dc.date.available 2018-09-18T20:31:32Z
dc.date.issued 2014
dc.identifier.issn 0036-0244
dc.identifier.uri https://dspace.kpfu.ru/xmlui/handle/net/140778
dc.description.abstract © 2014 Pleiades Publishing, Ltd. The Diels-Alder reaction between substituted anthracenes 1a-1j and 4-phenyl-1,2,4-triazoline-3,5 (2) is studied. In all cases except one, the reaction proceeds on the most active 9,10-atoms of substituted anthracenes. The orthogonality of the two phenyl groups at the 9,10-position of diene 1a is found to shield 9,10-reactive centers. No dienophiles with C=C bonds are shown to participate in the Diels-Alder reaction with 1a; however, the reaction 1a + 2 proceeds with the very active dienophile 2,4-phenyl-1,2,4-triazoline-3,5-dione. It is shown that attachment occurs on the less active but sterically accessible 1,4-reactive center of diene 1a. The structure of adduct 3a is proved by 1H and 13C NMR spectroscopy and X-ray diffraction analysis. The following parameters are obtained for reaction 1a + 2 ⇄ 3a in toluene at 25°C: Keq = 2120 M-1, ΔHf ≠ = 58.6 kJ/mol, ΔSf ≠ = -97 J/(mol K), ΔVf ≠ = -17.2 cm3/mol, ΔHb ≠ = 108.8 kJ/mol, ΔSb ≠ = 7.3 J/(mol K), ΔVb ≠ = -0.8 cm3/mol, ΔHr-n = -50.2 kJ/mol, ΔSr-n = -104.3 J/(mol K), ΔVr-n = -15.6 cm3/mol. It is concluded that the values of equilibrium constants of the reactions 1a-1j + 2 ⇄ 3a-3j vary within 4 × 101-1011 M-1.
dc.relation.ispartofseries Russian Journal of Physical Chemistry A
dc.subject 4-phenyl-1,2,4-triazoline-3,5-dione
dc.subject 9,10-diphenylanthracene
dc.subject Diels-Alder reaction
dc.subject high pressure
dc.subject regioselectivity
dc.title Features of the Diels-Alder reaction between 9,10-diphenylanthracene and 4-phenyl-1,2,4-triazoline-3,5-dione
dc.type Article
dc.relation.ispartofseries-issue 12
dc.relation.ispartofseries-volume 88
dc.collection Публикации сотрудников КФУ
dc.relation.startpage 2073
dc.source.id SCOPUS00360244-2014-88-12-SID84919754567


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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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