Hypervalent Iodine Reagent Mediated Reaction of [60]Fullerene with Amines

被引：27

作者：

Miao, Chun-Bao ^{[1
]}

Lu, Xin-Wei ^{[1
]}

Wu, Ping ^{[2
]}

Li, Jiaxing ^{[3
]}

Ren, Wen-Long ^{[1
]}

Xing, Meng-Lei ^{[1
]}

Sun, Xiao-Qiang ^{[1
]}

Yang, Hai-Tao ^{[1
]}

机构：

[1] Changzhou Univ, Sch Petrochem Engn, Changzhou 213164, Peoples R China

[2] Dezhou Univ, Coll Chem & Chem Engn, Key Lab Coordinat Chem & Funct Mat Univ Shandong, Dezhou 253023, Peoples R China

[3] Chinese Acad Sci, Inst Plasma Phys, Key Lab Novel Thin Film Solar Cells, Hefei 230031, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 23期

基金：

中国国家自然科学基金;

关键词：

ADDITION-REACTIONS; C-60; FULLERENE; FUNCTIONALIZATION; AMIDES; CYCLOADDITIONS; REARRANGEMENT; CYCLIZATION; RADICALS; ADDUCTS;

D O I：

10.1021/jo402079m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hypervalent iodine reagent mediated reaction of C-60 with various readily available amines for the easy preparation of iminofullerenes has been developed. The reaction between C-60 and sulfonamides can be effectively controlled to selectively synthesize azafulleroids or aziridinofullerenes under PhI(OAc)(2)/I-2 or PhIO/I-2/CuCl/lutidine conditions, respectively. For phosphamide and urea, only one isomer is obtained. However, carbamate gives three kinds of products. Interestingly, the reaction of C-60 with alkylamines allows the effective synthesis of aziridinofullerenes and regioselective cis-1-bisaziridinofullerenes.

引用

页码：12257 / 12262

页数：6

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