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Versatile Photorearrangement of Photocycloadducts from 5-Fluoro-1,3-dimethyluracil and Naphthalene
| Title: | Versatile Photorearrangement of Photocycloadducts from 5-Fluoro-1,3-dimethyluracil and Naphthalene |
| Authors: | Ohkura, Kazue Browse this author | | Akizawa, Hiromichi Browse this author | | Kudo, Mikiko Browse this author | | Ishihara, Tetsuya Browse this author | | Oshima, Nobuhiro Browse this author | | Seki, Koh-ichi Browse this author →KAKEN DB |
| Keywords: | Valence Isomerization | | Di-π-methane Rearrangement | | Benzopyrimidobarrelene | | Benzopyrimidosemibullvalene | | Naphthocyclobutapyrimidine |
| Issue Date: | 1-Jan-2012 |
| Publisher: | Japan Institute of Heterocyclic Chemistry |
| Journal Title: | Heterocycles |
| Volume: | 84 |
| Issue: | 2 |
| Start Page: | 1057 |
| End Page: | 1065 |
| Publisher DOI: | 10.3987/COM-11-S(P)83 |
| Abstract: | Direct UV-irradiation of 5-fluoro-1,3-dimethyluracil (5-FDMU) and naphthalene (1) with a 500 W high-pressure mercury lamp in a degassed Pyrex tube (λ > 300 nm) predominantly afforded benzopyrimidobarrelene derivative (2) through 1,4-addition, while irradiation in the presence of piperylene in singlet excited states preferentially afforded naphthocyclobuta-pyrimidine derivative (3) via 1,2-addition. Upon 254 nm light-irradiation of 2 gave rise to the formation of benzopyrimidosemibullvalene (4) in fair yields. The reaction pathway for the formation of 4 is reasonably explained in the terms of di-π-methane rearrangement. Adduct 3 was newly converted to the corresponding barrelene derivative (2) by long-wave-length irradiation in the presence of a triplet sensitizer. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/49042 |
| Appears in Collections: | アイソトープ総合センター (Central Institute of Isotope Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 関 興一
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