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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 185, 2010 - Issue 5-6: A Tribute to the Chemistry of Professor Naomichi Furukawa
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Original Articles

Chemical Modification of Endohedral Metallofullerene La@C82 with 3-chloro-3-phenyldiazirine

Midori O. Ishitsuka Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki, Japan
,
Haruka Enoki Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki, Japan
,
Takahiro Tsuchiya Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki, Japan
,
Zdenek Slanina Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki, Japan
,
Naomi Mizorogi Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki, Japan
,
Shigeru Nagase Department of Theoretical and Computational Molecular Science, Institute for Molecular Science, Okazaki, Aichi, Japan
,
Michael T. H. Liu Department of Chemistry, University of Prince Edward Island, Charlottetown, Prince Edward Island, Canada
&
Takeshi Akasaka Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki, Japan; Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki, Japan
 show all
Pages 1124-1130 | Received 18 Dec 2008, Accepted 13 Jan 2009, Published online: 27 May 2010
 
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Abstract

The photochemical reaction of an endohedral metalofullerene La@C82 with 3-chloro-3-phenydiazirine (3) affords the monoadduct as a phenylchlorocarbene (:CClPh) derivative. Spectroscopic analyses of UV-vis-near infrared and electron spin resonance and the theoretical calculations reveal that this monoadduct is a pair of stereoisomers with carbene substituents, and the carbene addition occurs regioselectively to the carbons having a high charge density and a high local strain of the C82 cage.

Acknowledgments

Dedicated to Professor Naomichi Furukawa on the occasion of his 70th birthday.We thank T. Wakahara for interesting discussions. This work was supported in part by a Grant-in-Aid and the 21st Century COE Program, Nanotechnology Support Project, The Next Generation Super Computing Project (Nanoscience Project), and Scientific Research on Priority Area from the Ministry of Education, Culture, Sports, Science, and Technology of Japan.

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