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Versatile Photorearrangement of Photocycloadducts from 5-Fluoro-1,3-dimethyluracil and Naphthalene

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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)

Submitter: 関 興一

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