1991 Fiscal Year Final Research Report Summary
Molecular Conversion of Photooxidation of Single Bond
| Project/Area Number |
02640378
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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 |
有機化学一般
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| Research Institution | University of Tsukuba |
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Principal Investigator |
AKASAKA Takeshi University of Tsukuba Department of Chemistry Associate Professor, 化学系, 助教授 (60089810)
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| Project Period (FY) |
1990 – 1991
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| Keywords | singlet oxygen / photooxidation / photosensitized oxygenation / cyclopropane / disilirane / dioxolane / disiladioxolane / active oxygen species |
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| Research Abstract |
The Photosensitized oxygenation(singlet oxygen oxidation)a variety of eletron rich olefins is known to afford the corresponding peroxides. However, none of photooxygenation of single bonds has been reported. In this project, we have developed a new type of reaction of singlet oxygen with single bonds.
Singlet oxygen oxidation of disilirajles and oxadisiliranes afforded the corresponding cyclic peroxides, derivatives of a novel class of cyclic peroxides. The reaction mechanism was elucidated by means of the results derived from trapping experiments, theoretical studies of the initially formed peroxidic intermediate, and stereochemical investigation.
Singlet oxygen oxidation of tetraanisylcylopropane gave the corresponding dioxolane quantitatively, demonstrating a first example of dioxygen insertion into a carbon-carbon single bond. The reaction mechanism was also discussed.
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