Efficient Alkylation Methods for the Synthesis of Hybrid Fluorocarbon-Hydrocarbon Tetrazoles as Potential Fluorinated Surfactants

被引:9
|
作者
Huang, Yangen [1 ]
Read, Roger W. [1 ]
Wang, Xiaobei [1 ]
机构
[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia
关键词
HUISGEN 1,3-DIPOLAR CYCLOADDITION; CLICK CHEMISTRY APPROACH; REGIOSELECTIVE SYNTHESIS; AZIDES; METHYLATION; POTASSIUM; SYSTEMS;
D O I
10.1071/CH10005
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first 1,5- and 2,5-disubstituted fluorous tetrazoles are sought as potential surfactants. Direct alkylation of monosubstituted tetrazoles using alkyl iodides and triflates is compared with the Mitsunobu reaction. Mitsunobu conditions provide advantage for perfluoroalkylethylation, in terms of selectivity towards the 2,5-isomers and overall yield, but are not applicable to perfluoroalkylmethylation.
引用
收藏
页码:802 / 807
页数:6
相关论文
共 50 条
  • [1] Synthesis of fluorinated epoxides opening the way to new hybrid fluorocarbon-hydrocarbon surfactants
    Pasc-Banu, A
    Petrov, O
    Perez, E
    Rico-Lattes, I
    Lattes, A
    Pozzi, G
    Quici, S
    SYNTHETIC COMMUNICATIONS, 2003, 33 (24) : 4321 - 4329
  • [2] Hybrid Fluorocarbon-Hydrocarbon Surfactants: Synthesis and Colloidal Characterization
    Grousson, Emilie
    Mahler, Florian
    Keller, Sandro
    Contino-Pepin, Christiane
    Durand, Gregory
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 14672 - 14683
  • [3] Micellar solution properties of fluorocarbon-hydrocarbon hybrid surfactants
    Ito, A
    Sakai, H
    Kondo, Y
    Yoshino, N
    Abe, M
    LANGMUIR, 1996, 12 (24) : 5768 - 5772
  • [4] Micelle aggregating condition of fluorocarbon-hydrocarbon hybrid surfactants in aqueous solution
    Ito, A
    Kamogawa, K
    Sakai, H
    Hamano, K
    Kondo, Y
    Yoshino, N
    Abe, M
    LANGMUIR, 1997, 13 (11) : 2935 - 2942
  • [5] Synthesis of phosphate-type fluorocarbon-hydrocarbon hybrid surfactants and their adsorption onto calcium hydroxyapatite
    Miyazawa, H
    Yokokura, H
    Ohkubo, Y
    Kondo, Y
    Yoshino, N
    JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (10) : 1485 - 1490
  • [6] Synthesis of phosphate-type fluorocarbon-hydrocarbon hybrid surfactants and their adsorption onto calcium hydroxyapatite
    Miyazawa, H
    Yokokura, H
    Ohkubo, Y
    Kondo, Y
    Yoshino, N
    JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (03) : 301 - 306
  • [7] Anisotropic reversed micelles with fluorocarbon-hydrocarbon hybrid surfactants in supercritical CO2
    Sagisaka, Masanobu
    Ono, Shinji
    James, Craig
    Yoshizawa, Atsushi
    Mohamed, Azmi
    Guittard, Frederic
    Enick, Robert M.
    Rogers, Sarah E.
    Czajka, Adam
    Hill, Christopher
    Eastoe, Julian
    COLLOIDS AND SURFACES B-BIOINTERFACES, 2018, 168 : 201 - 210
  • [8] Fluorocarbon-hydrocarbon hybrid cationic surfactants: Synthesis, surface-activity properties and anti-corrosion performance
    Nuer, Maimaiti
    Duan, Jiang
    Wei, Zengfeng
    Wu, Wenhai
    Ma, Jianxiang
    Zhang, Aidong
    JOURNAL OF MOLECULAR LIQUIDS, 2020, 306
  • [9] Synthesis and Properties of Fluorocarbon-Hydrocarbon Hybrid Block Copolymers with Perfluorosulfonimide Acid
    Hoshikawa, Naohiro
    Shinohara, Akihiro
    Hosokawa, Yoichi
    Hasegawa, Naoki
    Kawasumi, Masaya
    ACS OMEGA, 2020, 5 (43): : 27766 - 27773
  • [10] Hybrid fluorocarbon/hydrocarbon surfactants
    Kondo, Y
    Yoshino, N
    CURRENT OPINION IN COLLOID & INTERFACE SCIENCE, 2005, 10 (3-4) : 88 - 93