One-pot synthesis of new thio-derivatives of C60 with the unexpected formation of a thiazolidine-fulleropyrrolidine
One-pot synthesis of new thio-derivatives of C60 with the unexpected formation of a thiazolidine-fulleropyrrolidine
复制标题
一锅法合成新的 C60 硫代衍生物并意外形成噻唑烷-富勒吡咯烷
DOI：
10.1039/b9nj00420c
复制
发表时间：
2010
影响因子：
3.3
通讯作者：
Shangfeng Yang
中科院分区：
文献类型：
--
作者：
Chuanbao Chen;Xiaofang Li;Shangfeng Yang
C60 与氨基酸和醛的一锅普拉托反应得到五种新的富勒烯衍生物，包括两种意想不到的噻唑烷和恶唑烷富勒吡咯烷。特别是，L-半胱氨酸(1)、多聚甲醛和C60在回流甲苯溶液中通过1,3-偶极环加成反应提供了意想不到的新型噻唑烷-富勒吡咯烷衍生物3（而不是2），其结构得到了详细表征。提出了形成 3 的可能反应机制。这些表明1中S-H的活性氢对于3中噻唑烷环的形成至关重要。为了进一步证实这一结论，还研究了C60与不同氨基酸(5, 7)和醛(3-(甲硫基)丙醛(9)和2-噻吩醛(11))的反应，合成了C60的其他三种新硫代衍生物(6, 10, 12)以及恶唑烷富勒吡咯烷 (8)。
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).