Regio- and stereoselective [2+2] photocycloaddition in Ba2+ templated supramolecular dimers of styryl-derivatized aza-heterocycles. (April 2017)

• Record Type: Journal Article
• Authors: Berdnikova, Daria V.; Aliyeu, Tseimur M.; Delbaere, Stéphanie; Fedorov, Yuri V.; Jonusauskas, Gediminas; Novikov, Valentin V.; Pavlov, Alexander A.; Peregudov, Alexander S.; Shepel', Nikolay E.; Zubkov, Fedor I.; Fedorova, Оlga A.
• Is Part Of: Dyes and pigments. Volume 139(2017)
• Page Start: 397
• Page End: 402
• Publication Date: 2017-04
• Subjects: Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2016.11.053
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: The regio- and stereoselective [2+2] photocycloaddition of 15-crown-5-containing styrylheterocycles resulting in formation of only one cyclobutane isomer out of eleven possible is described. It was shown that the cycloaddition takes place solely in the case of the supramolecular preorganization of the reactive molecules provided by both π–π stacking interaction of the heterocyclic fragments and sandwich-type coordination of the crown ether residues by the barium cation. The results point out the importance of the supramolecular approach for the synthesis of cyclobutane derivatives with desired structure and conformation. Graphical abstract: Highlights: Formation of Ba 2+ templated "sandwich" dimers of crown-derivatized styrylheterocycles was studied. Supramolecular dimerization provides preorganization for regio- and stereoselective [2+2] photocycloaddition. The [2+2] photocycloaddition yields only one cyclobutane isomer out of eleven possible.