The Regioselectivity of Bingel-Hirsch Cycloadditions on Isolated Pentagon Rule Endohedral Metallofullerenes

被引：31

作者：

Garcia-Borras, Marc ^{[1
,2
]}

Ceron, Maira R. ^{[3
]}

Osuna, Silvia ^{[1
,2
]}

Izquierdo, Marta ^{[3
]}

Luis, Josep M. ^{[1
,2
]}

Echegoyen, Luis ^{[3
]}

Sola, Miquel ^{[1
,2
]}

机构：

[1] Univ Girona, IQCC, Campus Montilivi, Girona 17071, Catalonia, Spain

[2] Univ Girona, Dept Quim, Campus Montilivi, Girona 17071, Catalonia, Spain

[3] Univ Texas El Paso, Dept Chem, El Paso, TX 79968 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 07期

基金：

美国国家科学基金会;

关键词：

aromaticity; cage compounds; density-functional calculations; fullerenes; supramolecular chemistry; TRIMETALLIC NITRIDE CLUSTER; AROMATICITY; FULLERENE; REACTIVITY; SC3N-AT-C-78; DERIVATIVES; STABILITY; ADDUCTS; M=SC; C-60;

D O I：

10.1002/anie.201509057

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this work, the Bingel-Hirsch addition of diethylbromomalonate to all non-equivalent bonds of Sc3N@D-3h-C-78 was studied using density functional theory calculations. The regioselectivities observed computationally allowed the proposal of a set of rules, the predictive aromaticity criteria (PAC), to identify the most reactive bonds of a given endohedral metallofullerene based on a simple evaluation of the cage structure. The predictions based on the PAC are fully confirmed by both the computational and experimental exploration of the Bingel-Hirsch reaction of Sc3N@ D-5h-C-80,C- thus indicating that these rules are rather general and applicable to other isolated pentagon rule endohedral metallofullerenes.

引用

页码：2374 / 2377

页数：4

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