+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ PDF Full Text
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Translate
+ Recently Requested

Radical coupling reaction of paramagnetic endohedral metallofullerene La@C82

Radical coupling reaction of paramagnetic endohedral metallofullerene La@C82

Journal of the American Chemical Society 130(48): 16224-16230

The thermal reaction of La@C(82)(C(2v)) with 3-triphenylmethyl-5-oxazolidinone (1) in toluene affords benzyl monoadducts La@C(82)(C(2v))(CH(2)C(6)H(5)) (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))(CHClC(6)H(3)Cl(2)) (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))(C(2)H(4)NCPh(3)) (5), unlike the reaction in toluene.

(PDF emailed within 0-6 h: $19.90)

Accession: 055345743

Download citation: RISBibTeXText

PMID: 18998645

DOI: 10.1021/ja802748q

Related references

Stabilizing ion and radical ion pair states in a paramagnetic endohedral metallofullerene/π-extended tetrathiafulvalene conjugate. Journal of the American Chemical Society 134(39): 16103-6, 2012

Mechanistic study of the Diels-Alder reaction of paramagnetic endohedral metallofullerene: reaction of La@C82 with 1,2,3,4,5-pentamethylcyclopentadiene. Journal of the American Chemical Society 135(15): 5582-5587, 2013

Unprecedented chemical reactivity of a paramagnetic endohedral metallofullerene La@C(s)-C82 that leads hydrogen addition in the 1,3-dipolar cycloaddition reaction. Journal of the American Chemical Society 136(50): 17537-17546, 2014

A co-crystal composed of the paramagnetic endohedral metallofullerene La@C82 and a nickel porphyrin with high electron mobility. Angewandte Chemie 51(7): 1589-1591, 2012

Binding for endohedral-metallofullerene superatoms induced by magnetic coupling. Chemical Communications: -, 2018

Ferromagnetic spin coupling between endohedral metallofullerene La@C82 and a cyclodimeric copper porphyrin upon inclusion. Journal of the American Chemical Society 133(24): 9290-9292, 2011

Reactivity of endohedral metallofullerene la2@c80 in nucleophilic and electrophilic attacks: vibronic coupling density approach. Journal of Organic Chemistry 80(1): 141-147, 2014

Paramagnetic and theoretical study of Y₂@C₈₁N: an endohedral azafullerene radical. Dalton Transactions 43(34): 12871-5, 2014

Silver-mediated radical coupling reaction of isocyanides and alcohols/phenols in the presence of water: unprecedented hydration and radical coupling reaction sequence. Organic & Biomolecular Chemistry 15(7): 1580-1583, 2017

A Scandium Carbide Endohedral Metallofullerene: (Sc2 C2 )@C84. Angewandte Chemie 40(2): 397-399, 2018

Nanorods of endohedral metallofullerene derivative. Journal of the American Chemical Society 130(2): 450-451, 2007

The structural determination of endohedral metallofullerene Gd@C(82) by XANES. Chemical Communications: 474-476, 2008

Endohedral metallofullerene Sc3NC@C84: a theoretical prediction. Physical Chemistry Chemical Physics 14(43): 15099-15105, 2012

Biomedical activities of endohedral metallofullerene optimized for nanopharmaceutics. Journal of Nanoscience and Nanotechnology 10(12): 8610-8616, 2010

La3N@C92: An Endohedral Metallofullerene Governed by Kinetic Factors?. Inorganic Chemistry 55(7): 3302-3306, 2016