Functionalization of Fullerenes: Addition Reactions

Functionalization of Fullerenes: Addition Reactions
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富勒烯的功能化:加成反应

DOI:
10.1007/978-981-13-3242-5_33-1
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发表时间:
2021
期刊:
Handbook of Fullerene Science and Technology
影响因子:
--
通讯作者:
T. Akasaka
T. Akasaka
中科院分区:
--
文献类型:
--
作者:
M. Yamada;S. Nagase;T. Akasaka

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本章从富勒烯的亲核反应开始,其中格氏试剂、烷基锂和其他碳亲核试剂以及硅和磷亲核试剂已被用于合成各种富勒烯加合物。在某些情况下,多种加合物是区域选择性合成的。第二部分涉及亲电反应,尽管报道的这些反应的例子仍然有限。第三部分致力于加成-消除反应,该反应已被认为是构建亚甲基富勒烯的最有力的方法之一。其他类型的环加合物也可以通过修饰底物获得。卡宾和亚甲硅烷基也对富勒烯有反应性;这种反应性在第四部分中描述。第五部分综述了1,3-偶极环加成反应的研究进展,包括著名的普拉托反应。第六部分涉及氮烯加成,因为这些与1,3-偶极环加成有关。第七部分是膦介导的反应。值得注意的是,氮杂类富勒烯和氮杂甲烷富勒烯也已经通过1,3-偶极环加成,然后N2挤出制备。第八部分介绍了几个[2 + 2]环加成反应的例子。最后,在最后部分总结了各种Diels-Alder反应。值得注意的是,从富勒烯与含氮芳族化合物的反应中获得的一些Diels-Alder环加合物为制备开笼富勒烯和内嵌富勒烯提供了有用的前体。此外,利用C60与9,10-二甲基蒽的Diels-Alder反应的可逆性,实现了六元加合物的区域选择性合成。
This chapter begins with the nucleophilic reactions of fullerenes, in which Grignard reagents, alkyllithium, and other carbon nucleophiles, as well as silicon and phosphorous nucleophiles, have been employed for the synthesis of a variety of fullerene adducts. In some cases, multiple adducts have been synthesized regioselectively. The second part deals with electrophilic reactions, although reported examples of these reactions are still limited. The third part is devoted to addition–elimination reactions, which have been recognized as one of the most powerful methodologies to construct methanofullerenes. Other types of cycloadducts can also be obtained by modifying the substrates. Carbenes and silylenes are also reactive toward fullerenes; this reactivity is described in the fourth part. A variety of 1,3-dipolar cycloadditions, including the well-known Prato reactions, are summarized in the fifth part. The sixth part deals with nitrene additions, as these are relevant to 1,3-dipolar cycloadditions. The seventh part is devoted to phosphine-mediated reactions. Notably, azafulleroids and azamethanofullerenes have also been prepared via 1,3-dipolar cycloadditions followed by N2extrusion. Several examples of [2 + 2] cycloadditions are described in the eighth part. Finally, a variety of Diels–Alder reactions are summarized in the final part. Noteworthily, some Diels–Alder cycloadducts obtained from the reactions of fullerenes with nitrogen-containing aromatic compounds provide useful precursors for the preparation of open-cage fullerenes and endohedral fullerenes. In addition, the reversibility of the Diels–Alder reaction of C60with 9,10-dimethylanthracene has been applied to achieve the regioselective synthesis of hexaadducts.
氧化腈与[60]富勒烯的环加成
DOI: 10.1039/a606503a
发表时间: 1997
影响因子: 4.9
作者:
T. Ros;M. Prato;F. Novello;M. Maggini;M. Amici;C. D. Micheli
通讯作者: C. D. Micheli
DOI: 10.1002/anie.200905024
发表时间: 2010-01
期刊: Angewandte Chemie
影响因子: --
作者:
Xing Lu;Hidefumi Nikawa;T. Tsuchiya;T. Akasaka;M. Toki;H. Sawa;N. Mizorogi;S. Nagase
通讯作者: Xing Lu;Hidefumi Nikawa;T. Tsuchiya;T. Akasaka;M. Toki;H. Sawa;N. Mizorogi;S. Nagase
带有富勒烯取代基的叔膦和P-手性次膦酸酯
DOI: 10.1039/c39940002093
发表时间: 1994
期刊: Journal of The Chemical Society, Chemical Communications
影响因子: --
作者:
S. Yamago;M. Yanagawa;E. Nakamura
通讯作者: E. Nakamura
首次对富勒烯进行 X 射线结构测定 [2 2] Cycloadduct
DOI: --
发表时间: 1995
期刊:
影响因子: --
作者:
T. Ishida;Koji Shinozuka;T. Nogami;S. Sasaki;M. Iyoda
通讯作者: M. Iyoda
DOI: --
发表时间: 1994
期刊:
影响因子: --
作者:
S. Yamago;Atsuo Takeichi;E. Nakamura
通讯作者: E. Nakamura