Trifluoromethyl groups in crystal design of 1,4-diphenyl-1,3-butadienes for topochemical [2 + 2] photodimerization |
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Authors: | Liu Jin Wendt Natalie L Boarman Kelly J |
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Institution: | Department of Chemistry, Murray State University, Murray, Kentucky 42071, USA. jin.liu@murraystate.edu |
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Abstract: | structure: see text] UV irradiation of the powdered crystalline sample of each of three (E,E)-1,4-di(trifluoromethyl-substituted)phenyl-1,3-butadienes (1-3) was found to yield a single 2 + 2] cycloaddition product in the solid state. Moreover, upon irradiation, the crystalline samples of two (E,E)-1,4-di(trifluoromethyl- and fluorine-substituted)phenyl-1,3-butadienes (4, 5) undergo a similar conversion to afford a 2 + 2] cycloaddition product, respectively. Our observations suggest that trifluoromethyl groups can be used to direct 1,4-diphenyl-1,3-butadiene molecules to form a parallel, offset-stacked orientation suitable for topochemical 2 + 2] cycloaddition. |
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