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Stereospecific solid-state [2+2] autophotocycloaddition of a styryl dye containing a 18-crown-6 fragmentстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 18 июля 2013 г.
- Авторы: Vedernikov A.I., Gromov S.P., Lobova N.A., Kuz'mina L.G., Strelenko Y.A., Howard J.A.K, Alfimov M.V.
- Журнал: Russian Chemical Bulletin
- Том: 54
- Номер: 8
- Год издания: 2005
- Издательство: Springer Nature
- Местоположение издательства: Switzerland
- Первая страница: 1954
- Последняя страница: 1966
- DOI: 10.1007/s11172-006-0064-y
- Аннотация: A procedure was developed for the synthesis of a 18-crown-6-containing styryl dye of the pyridine series. Phototransformation products of the dye that formed upon irradiation with visible light in solution, films, and crystals were studied by H-1 and C-13 NMR spectroscopy and spectrophotometry. Irradiation of solutions of this dye in acetonitrile leads only to reversible E-Z photoisomerization of the C=C bond. Irradiation of a film of the dye induces stereospecific [2+2] photocycloaddition to form exclusively the rctt isomer of tetrasubstituted cyclobutane. The latter was found to undergo base-catalyzed isomerization giving rise to the rcct isomer. X-ray diffraction study showed that photocycloaddition occurs in single crystals without their destruction. The structures of the E isomer of the dye and the resulting rctt isomer of the cyclobutane derivative were established. The characteristic features of the molecular packing of the dye favorable for topochemical photocycloaddition in the crystal and the structural changes that accompany the cyclobutane formation are discussed.
- Добавил в систему: Громов Сергей Пантелеймонович