Syntheses and properties of dipyridylnorbornadienes.
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概要
- 論文の詳細を見る
2,3-Dipyridylnorbornadienes were prepared using the Diels–Alder reaction of the HBF<SUB>4</SUB> salts of dipyridylacetylenes with cyclopentadiene. Their absorptions extend to 380 nm and are red-shifted in an acidic media. They underwent photocyclization to give quadricyclanes which reverted to norbornadienes upon heating or encountering a Co(II)–TPP catalyst. 2,3-Bis(1-methylpyridinio)norbornadienes were also prepared by a Diels–Alder reaction of bis(1-methylpyridinio)acetylenes with cyclopentadiene. Irradiation of 1-methyl-2-pyridinio and 1-methyl-3-pyridinio derivatives led to the photostationary state between them and the corresponding quadricyclanes, while a 1-methyl-4-pyridinio derivative gave a water or methanol adduct in the presence of water or methanol. Electron-transfer reactions of bis(1-methylpyridinio)norbornadienes were investigated by cyclic voltammetry. The radical cations formed by their reduction were unstable compared with those of the corresponding <I>trans</I>-bis(1-methylpyridinio)ethylenes. Steric factors were shown to strongly affect the reactivities.
- 公益社団法人 日本化学会の論文
著者
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Yamashita Yoshiro
Department Of Biology Faculty Of Science Kumamoto University
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Takeda Yasuyuki
Department Of Chemistry Faculty Of Science Chiba University
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Miyashi Tsutomu
Department Of Chemistry Faculty Of Science Tohoku University
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Mukai Toshio
Department of Chemistry, Faculty of Science Tohoku University
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Hanaoka Takaaki
Department of Chemistry, Faculty of Science, Tohoku University
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Takeda Yasuyuki
Department of Chemistry, Faculty of Science, Tohoku University
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