Journal
TETRAHEDRON
Volume 66, Issue 48, Pages 9363-9369Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.10.006
Keywords
Aza[60]fullerene; Photoinduced electron transfer; Iminium cation; Benzyltrimethylsilanes; Electron-rich olefins
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Funding
- Greek Ministry of Education
- European Union
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Photolysis of (C59N)(2) solutions in the presence of neutral pi-donors, such as arenes and electron-rich alkenes leads to a series of novel aza[60]fullerene monoadducts. The key step of the reaction involves a photoinduced electron transfer from the donor molecule to the iminium cation of aza[60]fullerene, followed by radical coupling of the resulting aza[60]fullerenyl radical with an intermediate stabilized radical derived from the substrate. This type of reactivity has been proven efficient with arenes having oxidation potential higher than about 1.5 V. Simple olefins, such as tri- and tetra-methylethylene, as well as cyclohexene, can also participate in this kind of photoinduced electron transfer-initiated reaction with C59N+, affording the corresponding aza[60]fullerene derivatives. In the case of 2-methoxyprop-1-ene, 2,4-hexadiene, and beta,beta-dimethylstyrene, [2+2] cycloaddition reactions with the aza[60]fullerene carbon shell dominate, leading to a mixture of unidentified multiadducts. (C) 2010 Elsevier Ltd. All rights reserved.
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