Crown-ether styryl dyes |
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| Authors: | S P Gromov O A Fedorova E N Ushakov A V Buevich M V Alfimov |
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| Institution: | (1) N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 7a ul. Novatorov, 117421 Moscow, Russian Federation;(2) Institute of Chemical Physics in Chernogolovka, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation;(3) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation |
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| Abstract: | Styryl dyes (4a,b) containing a 15-crown-5 fragment and isomeric 2- and 4-quinolinium residues with anN-sulfopropyl substituent undergo 2+2]-autophotocycloaddition to give cyclobutane derivatives (9a,b) in acetonitrile only in the presence of Mg(ClO4)2 or Ca(ClO4)2. The stereospecificity of both pathways of photocycloaddition and its efficiency are explained by the preorganization of the supramolecular dimers derived from thetrans-isomers of the dyes when they are bound into complexes with Mg and Ca cations.For Part 14, see Ref. 1.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2225–2230, November, 1995.The work was carried out with financial support from the Russian Foundation for Basic Research (Project code 94-03-08531) and the International Science Foundation (Grants ISF, M8Q000 and N38000). |
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| Keywords: | crown ether styryl dyes complex-formation [2+2]-photocycloaddition cyclobutane derivatives 1H NMR spectra |
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