Abstract
Styryl dyes containing a crown ether group and a heteroaromatic moiety with a sulfoalkylN-substituent (1a,b) undergo photocyclodimerization in acetonitrile in the presence of Mg(ClO4)2 to give only the typeA isomer of cyclobutane derivative (2a,b). The photochemical regio- and stereoselectivity of the cycloaddition is explained by self-organization of thetrans-isomers of the styryl dyes upon complexation with the Mg2+ cations into dimers with a fixed mutual arrangement of multiple bonds.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
I. I. Baskin, K. Ya. Burshtein, A. A. Bagatur'yants, S. P. Gromov, and M. V. Alfimov,Dokl. Akad. Nauk, 1992,325, 306 [Dokl. Chem., 1992,325 (Engl. Transl.)].
J. A. Barltrop and J. D. Coule, inExcited States in Organic Chemistry, Wiley, Chichester, 1975.
M. Nógrádi, inStereochemistry, Akadémiai Kiadó, Budapest, 1981.
M. D. Cohen, B. S. Green, Z. Ludmer, and M. J. Schmidt,Chem. Phys. Lett., 1970,7, 486.
F. D. Lewis and R. H. Hirsch,Tetrahedron Lett, 1973, 4947.
M. V. Alfimov,Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 2197 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 2001 (Engl. Transl.)].
V. Ramamurthy,Tetrahedron, 1986,42, 5753.
J. M. Lehn,Angew. Chem. Int. Ed., 1988,27, 92.
S. P. Gromov, O. A. Fedorova, E. N. Ushakov, O. B. Stanislavskii, I. K. Lednev, and M. V. Alfimov,Dokl. Akad. Nauk SSSR, 1991,317, 1134 [Dokl. Chem., 1991,317 (Engl. Transl.)].
S. P. Gromov, O. A. Fedorova, E. N. Ushakov, O. B. Stanislavskii, and M. V. Alfimov,Dokl. Akad. Nauk SSSR, 1991,321, 104 [Dokl. Chem., 1991,321 (Engl. Transl.)].
E. N. Ushakov, O. B. Stanislavskii, S. P. Gromov, O. A. Fedorova, and M. V. Alfimov,Dokl. Akad. Nauk, 1992,323, 702 [Dokl. Chem., 1992,323 (Engl. Transl.)].
D. Donati, M. Fiorenza, and P. S. Fautoni,J. Heterocycl. Chem., 1979,16, 253.
M. A. Kirpichenok, L. M. Mel'nikova, L. K. Denisov, and I. I. Grandberg,Khim. Geterotsykl. Soed., 1988, 1169 [J. Heterocycl. Chem. USSR, 1988 (Engl. Transl.)].
K. B. Wiberg and D. E. Barth,J. Am. Chem. Soc.,91, 5124.
Author information
Authors and Affiliations
Additional information
For part 7, see ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1449–1452, August, 1993.
Rights and permissions
About this article
Cite this article
Alfimov, M.V., Gromov, S.P., Stanislavskii, O.B. et al. Crown-containing styryl dyes. Russ Chem Bull 42, 1385–1389 (1993). https://doi.org/10.1007/BF00699938
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00699938