笼内富勒烯 M3N@Ih-C80（M = Sc，Lu）上的双 1,3-偶极环加成反应：显著的笼内-簇区域化学控制。
Bis-1,3-dipolar Cycloadditions on Endohedral Fullerenes M3N@Ih-C80 (M = Sc, Lu): Remarkable Endohedral-Cluster Regiochemical Control.
机构信息
Department of Chemistry, University of Texas at El Paso , 500 West University Avenue, El Paso, Texas 79968, United States.
Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Universitat de Girona, Campus Montilivi, Facultat de Ciències , 17071 Girona, Spain.
出版信息
J Am Chem Soc. 2015 Sep 16;137(36):11775-82. doi: 10.1021/jacs.5b07207. Epub 2015 Sep 3.
In this work, we briefly report some attempts to control regioisomeric bisadditions on Sc3N@Ih-C80 and Lu3N@Ih-C80 using the tether-controlled multifunctionalization method. We then describe the use of independent (nontethered) bis-1,3-dipolar cycloaddition reactions and the characterization of 5 new bisadducts, 3 for Sc3N@C80 and 2 for Lu3N@C80, which have never been reported before. Unexpectedly and remarkably, 4 of these compounds exhibit relatively high symmetry and 2 of these bisadducts are the first examples of intrinsically chiral endohedral compounds, due to the addition pattern, not to the presence of chiral centers on the addends. Since an analysis of the statistically possible number of bisadduct isomers on an Ih-C80 cage has not been reported, we present it here.
在这项工作中，我们简要报告了一些使用 tether-controlled 多功能化方法控制 Sc3N@Ih-C80 和 Lu3N@Ih-C80 上区域异构体双加成的尝试。然后，我们描述了独立（无 tether）的双 1,3-偶极环加成反应的使用和 5 个新双加成物的表征，其中 3 个为 Sc3N@C80，2 个为 Lu3N@C80，以前从未报道过。出乎意料的是，这些化合物中有 4 个具有较高的对称性，其中 2 个双加成物是第一个内在手性笼内化合物的例子，这是由于加成模式，而不是由于添加物上存在手性中心。由于尚未报道 Ih-C80 笼上双加成物异构体的统计可能数量的分析，我们在此提出。
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