Photochemical and thermal reactions of a kinetically stabilized 9-silaanthracene: the first spectroscopic observation of a 9,10-Dewar-9-silaanthracene isomer |
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Authors: | Shinohara Akihiro Takeda Nobuhiro Tokitoh Norihiro |
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Institution: | Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan. |
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Abstract: | A kinetically stabilized 9-silaanthracene (1) underwent unique photochemical and thermal reactions to afford 9,10-Dewar-9-silaanthracene 2a and the head-to-tail 4 + 4] dimer 3, respectively. The structure of 2a was confirmed by 1H, 13C, and 29Si NMR spectra, and the kinetic parameters for the thermal reversion of 2a to 1 were obtained by the measurement of UV/vis spectra. The dimer 3 was thermally stable, and the molecular structure of 3 was determined by X-ray crystallographic analysis. It was experimentally demonstrated for the first time that 9-silaanthracene, as well as anthracene, can afford either the Dewar isomer or 4 + 4] dimer, depending on the reaction conditions. |
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