Bis-1,3-dipolar Cycloadditions on Endohedral Fullerenes M3N@Ih-C80 (M = Sc, Lu): Remarkable Endohedral-Cluster Regiochemical Control
Bis-1,3-dipolar Cycloadditions on Endohedral Fullerenes M3N@Ih-C80 (M = Sc, Lu): Remarkable Endohedral-Cluster Regiochemical Control
复制标题
DOI：
10.1021/jacs.5b07207
复制
发表时间：
2015-09-16
影响因子：
15
通讯作者：
Echegoyen, Luis
中科院分区：
文献类型：
--
作者：
Ceron, Maira R.;Izquierdo, Marta;Echegoyen, Luis
在这项工作中，我们简要地报告了一些尝试，以控制区域异构体的双加成在Sc 3 N @I-h-C-80和Lu 3 N @I-h-C-80使用栓控制的多官能化方法。然后，我们描述了使用独立的（非拴系）双-1，3-偶极环加成反应和5个新的双加成物的表征，3 Sc3N@C-80和2 Lu3N@C-80，这是以前从未报道过的。出乎意料的是，这些化合物中的4个表现出相对较高的对称性，这些双加合物中的2个是固有手性内面体化合物的第一个例子，这是由于加成模式，而不是由于在加成物上存在手性中心。由于统计学上可能的数量的双加合异构体的I-H-C-80笼的分析还没有报道，我们在这里介绍。
In this work, we briefly report some attempts to control regioisomeric bisadditions on Sc3N@I-h-C-80 and Lu3N@I-h-C-80 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@C-80 and 2 for Lu3N@C-80, 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 I-h-C-80 cage has not been reported, we present it here.