Stereospecific solid-state [2+2] autophotocycloaddition of a styryl dye containing a 18-crown-6 fragment
A.I. Vedernikov
1
,
S P Gromov
1
,
N.A. Lobova
1
,
L. G. Kuz'mina
2
,
Yu.A. Strelenko
3
,
J. A. K. Howard
4
,
M.V. Alfimov
1
Publication type: Journal Article
Publication date: 2005-08-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
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 1H and 13C 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.
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Vedernikov A. et al. Stereospecific solid-state [2+2] autophotocycloaddition of a styryl dye containing a 18-crown-6 fragment // Russian Chemical Bulletin. 2005. Vol. 54. No. 8. pp. 1954-1966.
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Vedernikov A., Gromov S. P., Lobova N., Kuz'mina L. G., Strelenko Y., Howard J. A. K., Alfimov M. Stereospecific solid-state [2+2] autophotocycloaddition of a styryl dye containing a 18-crown-6 fragment // Russian Chemical Bulletin. 2005. Vol. 54. No. 8. pp. 1954-1966.
Cite this
RIS
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TY - JOUR
DO - 10.1007/s11172-006-0064-y
UR - http://link.springer.com/10.1007/s11172-006-0064-y
TI - Stereospecific solid-state [2+2] autophotocycloaddition of a styryl dye containing a 18-crown-6 fragment
T2 - Russian Chemical Bulletin
AU - Vedernikov, A.I.
AU - Gromov, S P
AU - Lobova, N.A.
AU - Kuz'mina, L. G.
AU - Strelenko, Yu.A.
AU - Howard, J. A. K.
AU - Alfimov, M.V.
PY - 2005
DA - 2005/08/01
PB - Springer Nature
SP - 1954-1966
IS - 8
VL - 54
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2005_Vedernikov,
author = {A.I. Vedernikov and S P Gromov and N.A. Lobova and L. G. Kuz'mina and Yu.A. Strelenko and J. A. K. Howard and M.V. Alfimov},
title = {Stereospecific solid-state [2+2] autophotocycloaddition of a styryl dye containing a 18-crown-6 fragment},
journal = {Russian Chemical Bulletin},
year = {2005},
volume = {54},
publisher = {Springer Nature},
month = {aug},
url = {http://link.springer.com/10.1007/s11172-006-0064-y},
number = {8},
pages = {1954--1966},
doi = {10.1007/s11172-006-0064-y}
}
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MLA
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Vedernikov, A.I., et al. “Stereospecific solid-state [2+2] autophotocycloaddition of a styryl dye containing a 18-crown-6 fragment.” Russian Chemical Bulletin, vol. 54, no. 8, Aug. 2005, pp. 1954-1966. http://link.springer.com/10.1007/s11172-006-0064-y.
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