Isolation and characterization of [5,6]-pyrrolidino-Sc3N@Ih-C80 diastereomers

Yutaka Maeda; Masato Kimura; Chihiro Ueda; Michio Yamada; Toru Kikuchi; Mitsuaki Suzuki; Wei-Wei Wang; Naomi Mizorogi; Nikolaos Karousis; Nikos Tagmatarchis; Tadashi Hasegawa; Marilyn M. Olmstead; Alan L. Balch; Shigeru Nagase; Takeshi Akasaka

doi:10.1039/C4CC04946B

Isolation and characterization of [5,6]-pyrrolidino-Sc₃N@I_h-C₈₀ diastereomers†

Yutaka Maeda,*^a Masato Kimura,^b Chihiro Ueda,^a Michio Yamada,^a Toru Kikuchi,^a Mitsuaki Suzuki,^a Wei-Wei Wang,^c Naomi Mizorogi,^b Nikolaos Karousis,^d Nikos Tagmatarchis,^d Tadashi Hasegawa,^a Marilyn M. Olmstead,^e Alan L. Balch,^e Shigeru Nagase^c and Takeshi Akasaka*^abfg

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* Corresponding authors

^a Department of Chemistry, Tokyo Gakugei University, Koganei, Tokyo 184-8501, Japan
E-mail: ymaeda@u-gakugei.ac.jp

^b Life Science Center of Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki 305-8577, Japan
E-mail: akasaka@tara.tsukuba.ac.jp

^c Fukui Institute for Fundamental Chemistry, Kyoto University, Kyoto, Japan

^d Theoretical and Physical Chemistry Institute, National Hellenic Research Foundation, 48 Vassileos Constantinou Avenue, Athens 11635, Greece

^e Department of Chemistry, University of California at Davis, One Shields Ave, Davis, CA 95616, USA

^f College of Materials Science and Engineering, Huazhong University of Science and Technology, 430074 Wuhan, China

^g Foundation for Advancement of International Science, Tsukuba, Ibaraki 305-0821, Japan

Abstract

Reactions of Sc₃N@I_h-C₈₀ with aziridine derivatives were conducted to afford the corresponding mono-adducts. A pair of diastereomers of the mono-adduct [5,6]-pyrrolidino-Sc₃N@I_h-C₈₀ was isolated and characterized by means of mass spectrometry, vis-NIR absorption spectroscopy, and electrochemical measurements. Structural analysis of the mono-adducts was conducted by NMR and single-crystal X-ray structure determinations.

Chemical Communications

Isolation and characterization of [5,6]-pyrrolidino-Sc₃N@I_h-C₈₀ diastereomers†

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Isolation and characterization of [5,6]-pyrrolidino-Sc₃N@I_h-C₈₀ diastereomers

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