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具有混合八面体加成模式的碳的新型[3 : 2 : 1]六重加合物的顺序系链导向合成

Sequential Tether-Directed Synthesis of New [3 : 2 : 1] Hexakis-Adducts of C with a Mixed Octahedral Addition Pattern.

作者信息

Wachter Michael, Jurkiewicz Lisa, Hirsch Andreas

机构信息

Friedrich-Alexander Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058, Erlangen, Germany.

出版信息

Chemistry. 2021 May 17;27(28):7677-7686. doi: 10.1002/chem.202100319. Epub 2021 May 2.

DOI:10.1002/chem.202100319
PMID:33792116
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8251792/
Abstract

A new concept for the regioselective synthesis of [3 : 2 : 1] hexakis-adducts of fullerene C was developed. Based on sequential tether-directed remote functionalizations, chiral [3 : 2] pentakis-adducts with an incomplete octahedral addition pattern were synthesized via stepwise cyclopropanation of C with suitable macrocyclic tri- and bifunctional cyclomalonate tethers. The four resulting stereoisomers were isolated using chiral HPLC. The corresponding pairs of enantiomers show mirror image behavior in their CD-spectra. The pentakis-adducts served as suitable building blocks for the spatially controlled synthesis of mixed hexakis-adducts. Implementation of functional group-bearing monomalonates afforded octahedral [3 : 2 : 1] hexakis-adducts suitable for the construction of larger molecular and supramolecular fullerene architectures in excellent yield.

摘要

开发了一种用于区域选择性合成富勒烯C的[3 : 2 : 1]六加成物的新概念。基于连续的连接基导向远程官能团化，通过用合适的大环三官能和双官能环丙二酸连接基对C进行逐步环丙烷化反应，合成了具有不完全八面体加成模式的手性[3 : 2]五加成物。使用手性高效液相色谱法分离得到四种立体异构体。相应的对映体对在其圆二色光谱中表现出镜像行为。五加成物是用于空间控制合成混合六加成物的合适结构单元。带有官能团的单丙二酸酯的应用以优异的产率得到了适用于构建更大分子和超分子富勒烯结构的八面体[3 : 2 : 1]六加成物。

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