Nucleophilic substitution of alkylchlorodihydro[60]fullerenes: thermodynamic stabilities of alkylated C60 cation intermediates

Toshikazu Kitagawa; Yangsoo Lee; Masaaki Hanamura; Harumi Sakamoto; Hirofumi Konno; Ken’ichi Takeuchi; Koichi Komatsu

doi:10.1039/B210126B

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Nucleophilic substitution of alkylchlorodihydro[60]fullerenes: thermodynamic stabilities of alkylated C₆₀cation intermediates†

Toshikazu Kitagawa,*^a Yangsoo Lee,^a Masaaki Hanamura,^b Harumi Sakamoto,^b Hirofumi Konno,^a Ken’ichi Takeuchi^b and Koichi Komatsu*^a

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* Corresponding authors

^a Institute for Chemical Research, Kyoto University, Uji, Kyoto, Japan
E-mail: kitagawa@scl.kyoto-u.ac.jp
Fax: 81 774 38 3178
Tel: 81 774 38 3173

^b Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Sakyo-ku, Kyoto, Japan

Abstract

Thermodynamic stabilities of alkylated C₆₀ cations (RC₆₀⁺) were determined based on the activation free energies of S_N1 solvolysis of the title compounds, indicating that these cations have stabilities comparable to that of the tert-butyl cation.

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Supplementary files

Selected spectral data for newly synthesized compounds DOC (173K)

Article information

DOI: https://doi.org/10.1039/B210126B
Article type: Communication
Submitted: 16 Oct 2002
Accepted: 07 Nov 2002
First published: 20 Nov 2002

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Chem. Commun., 2002, 3062-3063

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Nucleophilic substitution of alkylchlorodihydro[60]fullerenes: thermodynamic stabilities of alkylated C₆₀ cation intermediates

T. Kitagawa, Y. Lee, M. Hanamura, H. Sakamoto, H. Konno, K. Takeuchi and K. Komatsu, Chem. Commun., 2002, 3062 DOI: 10.1039/B210126B

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