Synthetic Application of Photochemical Electron Transfer in Solvents with Relatively Low Polarity.
| Project/Area Number |
01550655
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機工業化学
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| Research Institution | Miyasaki University |
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Principal Investigator |
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| Co-Investigator(Kenkyū-buntansha) |
NAKABAYASHI Kenichi 宮崎大学, 教育学部, 講師 (60201670)
YASUDA Masahide 宮崎大学, 工学部, 助教授 (00174516)
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| Project Period (FY) |
1989 – 1990
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| Project Status |
Completed (Fiscal Year 1990)
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| Budget Amount *help |
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1990: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1989: ¥1,500,000 (Direct Cost: ¥1,500,000)
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| Keywords | Photochemical Electron Transfer / Photoamination / Arenes / Solvent with Relatively Low Polarity / Ring-Cleavage Reactions / Oxetanes, / Exciplexes |
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| Research Abstract |
(1) The photoamination of phenanthrene with propylamine in the presence of p-dicyanobenzene was investigated in solvents with relatively low polarity such as 1, 2-dimethoxyethane, tetrahydrofuran, and 1, 4-dioxane. The photoamination in the presence of Et_4NBF_4 occurred to give 9-proplyamino-9, 10-dihydrophenanthrene, while photoamination in the absence of the salt did not occur al all. We assume the mechanism for the photoamination via salt-induced charge separation of the exciplexes between phenanthrene and p-dicyanobenzene into ion radicals.
Also, the photoamination of naphthalenes, 2, 3-dimethylnaphthalene, and anthracene proceeded in the presence of the salt to give aminated products.
(2) The stereochemistry of the photoamination was elucidated for phenanthrene derivatives. It is found that the amine and ammonia add to the arenes in the trans manner predominantly. The stereoselectivities of amination did not depend on solvent polarity.
(3) Photochemical rig-cleavage reaction of 2, 2-diaryloxetanes in the presence of triethylamine proceeded in hexane to give 1, 1-diarylethenes selectively. The photoreaction was suggested to occur via exciplex between the oxetane and triethylamine.
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Report
(3 results)
Research Products
(17 results)
