Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 48, Pages 16224-16230Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja802748q
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Funding
- 21st Century COE Program
- Nanotechnology Support Project
- The Next Generation Super Computing Project (Nanoscience Project)
- Ministry of Education, Culture, Sports, Science, and Technology of Japan
- Kurata Memorial Hitachi Science and Technology Foundation
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The thermal reaction of La@C-82(C-82) with 3-triphenylmethyl-5-oxazolidinone (1) in toluene affords benzyl monoadducts La@C-82(C-2v)(CH2C6H5) (2a-2d). The same monoadducts are also obtained by the photoirradiation of La@C-82(C-2v) in toluene without the existence of 1. These reactions are applicable to paramagnetic metallofullerenes, such as La@C-82(C-s) and Ce@C-82(C-2v). The photoirradiation of La@C-82(C-2v) in 1,2-dichlorobenzene in the presence of alpha,alpha,2,4-tetrachlorotoluene also affords the monoadducts La@C-82(C-2v)(CHClC6H3Cl2) (3a-3d). The monoadducts are fully characterized by spectroscopic analyses. Single-crystal X-ray structure analysis for 3d reveals the unique structure. Theoretical calculations show that the cage carbons having high,spin densities are selectively attacked by radical species to form the monoadducts linked by a carbon-carbon single bond. The thermal reaction of La@C-82(C-2v) with 1 in benzene affords metallofulleropyrrolidine La@C-82(C-2v)(C2H4NCPh3) (5), unlike the reaction in toluene.
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