Issue 2, 2010
From the journal:

New Journal of Chemistry

One-pot synthesis of new thio-derivatives of C60 with the unexpected formation of a thiazolidine-fulleropyrrolidine†

Chuanbao Chen,a   Xiaofang Lib  and  Shangfeng Yang*a  

* Corresponding authors

a Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Materials for Energy Conversion & Department of Materials Science and Engineering, University of Science and Technology of China (USTC), Hefei 230026, China
E-mail: sfyang@ustc.edu.cn
Fax: +86 (551)3601 750
Tel: +86 (551)3601 750

b School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201, China

Abstract

One-pot Prato reactions of C60 with amino acids and aldehydes afford five new fullerene derivatives, including two unexpected thiazolidine and oxazolidine fulleropyrrolidines. In particular, L-cysteine (1), paraformaldehyde and C60 in refluxing toluene solution affords an unexpected new thiazolidine-fulleropyrrolidine derivative 3 (instead of 2) via 1,3-dipolar cycloaddition, whose structure was characterized in detail. A possible reaction mechanism for the formation of 3 is proposed. These suggest that the active hydrogen of S–H in 1 is essential for the formation of the thiazolidine ring in 3. To confirm further this conclusion, reactions of C60 with different amino acids (5, 7) and aldehydes (3-(methylthio)proplonaldehyde (9) and 2-thiophenaldehyde (11)) were also studied, resulting in the synthesis of other three new thio-derivatives of C60 (6, 10, 12) as well as an oxazolidine fulleropyrrolidine (8).

Graphical abstract: One-pot synthesis of new thio-derivatives of C60 with the unexpected formation of a thiazolidine-fulleropyrrolidine

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Article information

DOI
https://doi.org/10.1039/B9NJ00420C
Article type
Paper
Submitted
20 Aug 2009
Accepted
28 Oct 2009
First published
09 Dec 2009

New J. Chem., 2010,34, 331-336

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One-pot synthesis of new thio-derivatives of C60 with the unexpected formation of a thiazolidine-fulleropyrrolidine

C. Chen, X. Li and S. Yang, New J. Chem., 2010, 34, 331 DOI: 10.1039/B9NJ00420C

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