Fullerenyl azide: synthesis and reactivity

被引：7
|
作者：
Jiang, Zhongping [1 ]
Xiao, Zuo [1 ]
Zhang, Gaihong [1 ]
Gan, Liangbing [1 ,2 ]
Wang, Dian [1 ]
Zhang, Wenxiong [1 ]
机构：
[1] Peking Univ, Coll Chem & Mol Engn, Beijing Natl Lab Mol Sci, Minist Educ,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 02期
关键词：
1,3-DIPOLAR CYCLOADDITION; CLICK CHEMISTRY; DERIVATIVES; ALKYNE;
D O I：
10.1016/j.tetlet.2009.11.032
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Trimethylsilyl azide adds to the carbonyl carbon in a cage-opened fullerene derivative to form the first fullerenyl azide compoung. The fullerene-bound azido group exhibits some unusual reactivity compared with that exhibited by other organic azido compounds. Heating the azidofullerene at 100 degrees C only led to the cleavage of peroxo groups in the compound, whereas the azido group remained unchanged. Triphenylphosphine reacted with the azido group to form isolable iminophosphorane, which could not be hydrolyzed under normal acidic and basic conditions. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：415 / 417
页数：3
相关论文
共 50 条
  • [31] Clickable azide-functionalized bromoarylaldehydes - synthesis and photophysical characterization
    Goebel, Dominik
    Friedrich, Marius
    Lork, Enno
    Nachtsheim, Boris J.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 1683 - 1692
  • [32] Alkyne-azide click chemistry mediated carbanucleosides synthesis
    Broggi, Julie
    Joubert, Nicolas
    Aucagne, Vincent
    Berteina-Raboin, Sabine
    Diez-Gonzalez, S.
    Nolan, Steve
    Topalis, Dimitri
    Deville-Bonne, Dominique
    Balzarini, Jan
    Neyts, Johan
    Andrei, Graciela
    Snoeck, Robert
    Agrofoglio, Luigi A.
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (10-12) : 1391 - 1394
  • [33] Synthesis and reactivity of organopolypalladium complexes
    Murahashi, T
    Kurosawa, H
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2003, 61 (07) : 652 - 660
  • [34] The Cyanamide Moiety, Synthesis and Reactivity
    Larraufie, Marie-Helene
    Maestri, Giovanni
    Malacria, Max
    Ollivier, Cyril
    Fensterbank, Louis
    Lacote, Emmanuel
    SYNTHESIS-STUTTGART, 2012, 44 (09): : 1279 - 1292
  • [35] Lewis base adducts of diisobutylaluminum azide: synthesis and thermal stability
    Bennae, Kenneth T.
    Powell, Douglas R.
    Wehmschulte, Rudolf J.
    JOURNAL OF COORDINATION CHEMISTRY, 2015, 68 (14) : 2470 - 2479
  • [36] Synthesis and reactivity of β-stannylated phenylalanines
    Doelling, Karin
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2018, 73 (01): : 3 - 16
  • [37] Reactivity of indolizines in organic synthesis
    Elattar, Khaled M.
    Youssef, Ibrahim
    Fadda, Ahmed A.
    SYNTHETIC COMMUNICATIONS, 2016, 46 (09) : 719 - 744
  • [38] Synthesis and reactivity of fluorinated heterocycles
    Luzzio, Frederick A.
    ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 132, 2020, 132 : 1 - 84
  • [39] Synthesis of Bioactive 1,2,3-Triazole-Fused Macrocycles via Azide-Alkyne Cycloaddition
    Jahan, Nasrin
    Pal, Arkadip
    Ansary, Inul
    SYNOPEN, 2024, 08 (01): : 1 - 38
  • [40] Manipulating the Click Reactivity of Dibenzoazacyclooctynes: From Azide Click Component to Caged Acylation Reagent by Silver Catalysis
    Shi, Wei
    Tang, Feng
    Ao, Jiwei
    Yu, Qun
    Liu, Junjie
    Tang, Yubo
    Jiang, Bofeng
    Ren, Xuelian
    Huang, He
    Yang, Weibo
    Huang, Wei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (45) : 19940 - 19944
12345