Abstract
A quaternary 4-styrylpyridinium salt having the N-ammoniopropyl substituent forms a pseudodimeric head-to-tail complex with neutral 18-crown-6-containing 4-styrylpyridine in MeCN through H-bonding. This complex undergoes stereospecific [2+2] photocycloaddition due to preorganization of the ethylene bonds in the syn-arranged chromophoric fragments of the components. The structure of the rctt-isomer of the cyclobutane derivative obtained was established by NMR spectroscopy and X-ray diffraction analysis.
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References
R. Vilar, Structure and Bonding, 2004, 111, 85.
G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev., 2008, 108, 1.
S. P. Gromov, Ros. nanotekhnologii [Nanotechnologies in Russia], 2006, 1, No. 1–2, 29 (in Russian).
S. P. Gromov, E. N. Ushakov, A. I. Vedernikov, N. A. Lobova, M. V. Alfimov, Yu. A. Strelenko, J. K. Whitesell, M. A. Fox, Org. Lett., 1999, 1, 1697.
S. P. Gromov, A. I. Vedernikov, E. N. Ushakov, N. A. Lobova, A. A. Botsmanova, S. S. Basok, L. G. Kuz’mina, A. V. Churakov, Yu. A. Strelenko, M. V. Alfimov, E. I. Ivanov, J. A. K. Howard, D. Johnels, U. G. Edlund, New J. Chem., 2005, 29, 881.
A. I. Vedernikov, E. N. Ushakov, N. A. Lobova, A. A. Kiselev, M. V. Alfimov, S. P. Gromov, Izv. Akad. Nauk. Ser. Khim., 2005, 656 [Russ. Chem. Bull., Int. Ed., 2005, 54, 666].
A. I. Vedernikov, N. A. Lobova, E. N. Ushakov, M. V. Alfimov, S. P. Gromov, Mendeleev Commun., 2005, 15, 173.
S. P. Gromov, A. I. Vedernikov, N. A. Lobova, L. G. Kuz’mina, S. N. Dmitrieva, O. V. Tikhonova, M. V. Alfimov, Pat. RF 2278134; Byul. izobret. [Bull. Invent.], 2006, No. 17 (in Russian).
A. I. Vedernikov, D. V. Kondratuk, N. A. Lobova, T. M. Valova, V. A. Barachevskii, M. V. Alfimov, S. P. Gromov, Mendeleev Commun., 2007, 17, 264.
A. I. Vedernikov, S. K. Sazonov, P. S. Loginov, N. A. Lobova, M. V. Alfimov, S. P. Gromov, Mendeleev Commun., 2007, 17, 29.
J. L. R. Williams, R. E. Adel, J. M. Carlson, G. A. Reynolds, D. G. Borden, J. A. Ford, J. Org. Chem., 1963, 28, 387.
A. I. Vedernikov, S. P. Gromov, N. A. Lobova, L. G. Kuz’mina, Yu. A. Strelenko, J. A. K. Howard, M. V. Alfimov, Izv. Akad. Nauk. Ser. Khim., 2005, 1896 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1954].
L. G. Kuz’mina, A. I. Vedernikov, N. A. Lobova, A. V. Churakov, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, New J. Chem., 2007, 31, 980.
C. Frassineti, S. Ghelli, P. Gans, A. Sabatini, M. S. Moruzzi, A. Vacca, Anal. Biochem., 1995, 231, 374.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1893–1899, September, 2009.
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Vedernikov, A.I., Sazonov, S.K., Kuz’mina, L.G. et al. Stereospecific [2+2] photocycloaddition in a pseudodimeric complex between N-ammoniopropylstyrylpyridine and 18-crown-6-containing styrylpyridine. Russ Chem Bull 58, 1955–1961 (2009). https://doi.org/10.1007/s11172-009-0267-0
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DOI: https://doi.org/10.1007/s11172-009-0267-0