期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 10, 页码 6551-6566出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00544
关键词
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资金
- JSPS KAKENHI [16H06193, 17K19221]
- Grants-in-Aid for Scientific Research [16H06193, 17K19221] Funding Source: KAKEN
Radical cation vinylcyclopropane rearrangements by TiO2 photo-catalysis 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.
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