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
  • [1] Synthesis of fullerenyl-1,2,3-triazoles by reaction of fullerenyl azide with terminal acetylenes
    Sadretdinova, Zarema R.
    Akhmetov, Arslan R.
    Tulyabaev, Artur R.
    Budnikova, Yulia H.
    Dudkina, Yulia B.
    Tuktarov, Airat R.
    Dzhemilev, Usein M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (42) : 9299 - 9305
  • [2] Synthesis of Benzothieno[60]fullerenes through Fullerenyl Cation Intermediates
    Matsuo, Yutaka
    Yu, Yun
    Yang, Xiao-Yu
    Ueno, Hiroshi
    Okada, Hiroshi
    Shibuya, Hiromasa
    Choi, Yeong Suk
    Jin, Yong Wan
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10) : 6270 - 6277
  • [3] Fullerenyl Boronic Esters: Ferric Perchlorate-Mediated Synthesis and Functionalization
    Li, Fa-Bao
    You, Xun
    Liu, Tong-Xin
    Wang, Guan-Wu
    ORGANIC LETTERS, 2012, 14 (07) : 1800 - 1803
  • [4] Synthesis of Azide Polymers
    Li Guang
    Bai Ruke
    PROGRESS IN CHEMISTRY, 2011, 23 (08) : 1692 - 1699
  • [5] An Azide-Functionalized Nitronyl Nitroxide Radical: Synthesis, Characterization and Staudinger-Bertozzi Ligation Reactivity
    Barbon, Stephanie M.
    Gobbo, Pierangelo
    Luo, Wilson
    Price, Jacquelyn T.
    Biesinger, Mark C.
    Workentin, Mark S.
    Gilroy, Joe B.
    SYNLETT, 2016, 27 (02) : 304 - 308
  • [6] Structural Determinants of Alkyne Reactivity in Copper-Catalyzed Azide-Alkyne Cycloadditions
    Zhang, Xiaoguang
    Liu, Peiye
    Zhu, Lei
    MOLECULES, 2016, 21 (12)
  • [7] Facile preparation of fullerenyl boronic esters
    Dai, Zhifei
    Jiang, Zhongping
    Zhang, Gang
    Xin, Nana
    Gan, Liangbing
    TETRAHEDRON, 2012, 68 (26) : 5193 - 5196
  • [8] Synthesis of a library of glucal-derived triazoles via copper-catalyzed azide-alkyne cyclization
    Shamim, Anwar
    Souza, Frederico B.
    Vasconcelos, Stanley N. S.
    Stefani, Helio A.
    TETRAHEDRON LETTERS, 2017, 58 (09) : 884 - 888
  • [9] Synthesis of polynorbornene with pendant moiety bearing azide and terminal alkyne groups
    Zhang, Ze
    Peng, Zhi Wei
    Fan, Kun Zeng
    CHINESE CHEMICAL LETTERS, 2011, 22 (07) : 785 - 788
  • [10] Synthesis and Characterization of a 2,6-Diiminophenylgermanium(II) Hydroxide, Azide, and Triazaphospole
    Chia, Siew-Peng
    Li, Yongxin
    So, Cheuk-Wai
    ORGANOMETALLICS, 2013, 32 (18) : 5231 - 5234
12345