A pirouette on a metallofullerene sphere:: Interconversion of isomers of N-tritylpyrrolidino Ih Sc3N@C80
A pirouette on a metallofullerene sphere:: Interconversion of isomers of N-tritylpyrrolidino Ih Sc3N@C80
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DOI：
10.1021/ja0601843
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发表时间：
2006-05-17
影响因子：
15
通讯作者：
Dorn, Harry C.
中科院分区：
文献类型：
--
作者：
Cai, Ting;Slebodnick, Carla;Dorn, Harry C.
将Sc3N@ C80的纯I-h异构体通过相应的亚甲酰基与n -三苯基甲基- 5-恶唑烷酮反应。反应生成两种单加合物；一个（1b）是动力学产物，另一个（1a）在热力学上更稳定。还形成了少量的双聚体。核磁共振光谱和x射线晶体学证实了热力学单加合物1a的结构是由横跨5,6环结的加成引起的。通过核磁共振实验和x射线晶体学分析，证实了产物1b为6,6环接合加合物。在回流中，纯氯苯1b转化为热力学更稳定的1a异构体。这些n -三烷基吡咯烷酮衍生物是潜在的有用的前体化合物，可用于进一步衍生化的各种应用。
The pure I-h isomer of Sc3N@ C80 was allowed to react with N-triphenylmethyl- 5- oxazolidinone via the corresponding azomethine ylide. The reaction results in the formation of two monoadducts; one (1b) is the kinetic product, and the other (1a) is thermodynamically more stable. Small amounts of the bisadducts were also formed. The structure of the thermodynamic monoadduct 1a was shown conclusively by NMR spectroscopy and X-ray crystallography to result from addition across the 5,6-ring junction. The kinetic product 1b was demonstrated to be the 6,6-ring juncture adduct on the basis of NMR experiments and X-ray crystallography. In refluxing chlorobenzene pure 1b was converted to the more thermodynamically stable 1a isomer. These N-tritylpyrrolidino derivatives are potentially useful precursor compounds for further derivatization for various applications.