X-ray crystallographic analysis of N,N-diallylcoumarincarboxamides and the solid-state photochemical reaction |
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Authors: | Masami Sakamoto Mamoru Kato Eishi Oda Shuichiro Kobaru Takashi Mino Tsutomu Fujita |
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Affiliation: | Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan |
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Abstract: | X-ray crystallographic analysis and the photochemical aspects of N,N-diallylcoumarincarboxamides were investigated. Irradiation of the corresponding amides promoted stereoselective intramolecular cyclobutane formation exclusively. The solid-state photoreaction of the coumarinamide without substituent on the 4-position proceeded in a crystal-to-crystal manner. On the other hand, photolysis of the amide possessing a methyl group at the 4-position also effected 2+2 cycloaddition; however, the reaction proceeded much slower. The difference in the reactivity was explainable on the basis of the molecular conformation in the crystal lattice. |
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Keywords: | Coumarincarboxamide derivatives Solid-state reaction 2+2 Cycloaddition X-ray crystallography Photochemical reaction |
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