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Stereospecific [2+2] autophotocycloaddition in the dimeric complex of 18-crown-6 ether styryl dye bearing N-(3-ammoniopropyl) substituent |
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| Authors: | S P Gromov N A Lobova A I Vedernikov L G Kuz’mina J A K Howard M V Alfimov |
| Institution: | 1. Photochemistry Center, Russian Academy of Sciences, 7A ul. Novatorov, 119421, Moscow, Russian Federation 2. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991, Moscow, Russian Federation 3. Department of Chemistry, University of Durham, South Road, Durham, DH1 3LE, UK |
| Abstract: | New 18-crown-6 ether styryl dye of the 4-pyridine series bearing N-(3-ammoniopropyl) substituent has been synthesized. In MeCN, the dye forms a stable dimeric complex of the syn-head-to-tail type due to the complexation of the ammonium group of one molecule with the crown ether fragment of another. In the dimeric complex, the ethylene bonds of the molecules are close in space and antiparallel, which promotes an efficient stereospecific 2+2] autophotocycloaddition to yield the only rctt-isomer of 1,2,3,4-tetrasubstituted cyclobutane. The cyclobutane derivative structure was confirmed by NMR spectroscopy and X-ray diffraction. |
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