Radical-Cation Vinylcyclopropane Rearrangements by TiO2 Photocatalysis
Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations...
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| Veröffentlicht in: | Journal of organic chemistry 2020-05, Vol.85 (10), p.6551-6566 |
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| container_end_page | 6566 |
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| container_title | Journal of organic chemistry |
| container_volume | 85 |
| creator | Maeta, Naoya Kamiya, Hidehiro Okada, Yohei |
| description | Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. A stepwise mechanism via distonic radical cations is proposed based on preliminary mechanistic studies, which is supported by density functional theory calculations. |
| doi_str_mv | 10.1021/acs.joc.0c00544 |
| format | Article |
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The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. 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Org. Chem</addtitle><description>Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. 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Org. Chem</addtitle><date>2020-05-15</date><risdate>2020</risdate><volume>85</volume><issue>10</issue><spage>6551</spage><epage>6566</epage><pages>6551-6566</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. 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| source | ACS Publications |
| title | Radical-Cation Vinylcyclopropane Rearrangements by TiO2 Photocatalysis |
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