An air-stable radical with a redox-chameleonic amide

被引:7
|
作者
Peltier, Jesse L. [1 ]
Serrato, Melinda R. [1 ]
Thery, Valentin [2 ]
Pecaut, Jacques [3 ]
Tomas-Mendivil, Eder [2 ]
Bertrand, Guy [1 ]
Jazzar, Rodolphe [1 ]
Martin, David [2 ]
机构
[1] Univ Calif San Diego, Dept Chem & Biochem, UCSD CNRS Joint Res Chem Lab IRL 3555, La Jolla, CA 92093 USA
[2] Univ Grenoble Alpes, DCM, CNRS, F-38000 Grenoble, France
[3] Univ Grenoble Alpes, INAC SyMMES, CNRS, CEA,UMR 5819, F-38000 Grenoble, France
关键词
SELECTIVE PHOTOCYCLIZATION; AMINO-ACIDS; CARBENES; STABILITY; 2-QUINUCLIDONIUM; REACTIVITY; COMPLEXES; OXIDATION; METALS; CATION;
D O I
10.1039/d2cc05404c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An air-stable (amino)(amido)radical was synthesized by reacting a cyclic (alkyl)(amino)carbene with carbazoyl chloride, followed by one-electron reduction. We show that an adjacent radical center weakens the amide bond. It enables the amino group to act as a strong acceptor under steric contraint, thus enhancing the stabilizing capto-dative effect.
引用
收藏
页码:595 / 598
页数:4
相关论文
共 50 条
  • [41] Hiding and recovering electrons in a dimetallic endohedral fullerene: Air-stable products from radical additions
    Akasaka, Takeshi (akasaka@tara.tsukuba.ac.jp), 1600, American Chemical Society (137):
  • [42] A tunable lanthanide cubane platform incorporating air-stable radical ligands for enhanced magnetic communication
    Gabriel Brunet
    Milad Hamwi
    Maykon A. Lemes
    Bulat Gabidullin
    Muralee Murugesu
    Communications Chemistry, 1
  • [43] Photo-Induced Ultrafast Charge Transfer and Air-Stable Radical Formation in Tetraphenylpyrene Derivatives
    Tang, Lu
    Gao, Yuhang
    Cong, Nannan
    Cui, Zhiyuan
    Zhang, Ming
    Li, Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (02)
  • [44] A tunable lanthanide cubane platform incorporating air-stable radical ligands for enhanced magnetic communication
    Brunet, Gabriel
    Hamwi, Milad
    Lemes, Maykon A.
    Gabidullin, Bulat
    Murugesu, Muralee
    COMMUNICATIONS CHEMISTRY, 2018, 1
  • [45] Hiding and Recovering Electrons in a Dimetallic Endohedral Fullerene: Air-Stable Products from Radical Additions
    Yamada, Michio
    Kurihara, Hiroki
    Suzuki, Mitsuaki
    Saito, Masayoshi
    Slanina, Zdenek
    Uhlik, Filip
    Aizawa, Toshihiro
    Kato, Tatsuhisa
    Olmstead, Marilyn M.
    Balch, Alan L.
    Maeda, Yutaka
    Nagase, Shigeru
    Lu, Xing
    Akasaka, Takeshi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) : 232 - 238
  • [46] SYNTHESIS OF AN AIR-STABLE, MOISTURE-STABLE, AND THERMALLY STABLE TUNGSTEN(VI) OXO ALKYLIDENE COMPLEX - PRECURSOR TO AN AIR-STABLE AND MOISTURE-STABLE ROMP CATALYST
    BLOSCH, LL
    ABBOUD, K
    BONCELLA, JM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) : 7066 - 7068
  • [47] (Ferrocenylmethyl)phosphine, an air-stable primary phosphine
    Goodwin, NJ
    Henderson, W
    Nicholson, BK
    Fawcett, J
    Russell, DR
    JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (11): : 1785 - 1793
  • [48] Novel synthesis of air-stable FeCo nanoparticles
    Chaubey, Girija S.
    Poudyal, Narayan
    Rong, Chuanbing
    Liu, J. P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 454 - 454
  • [49] Air-stable phosphine organocatalysts for the hydroarsination reaction
    Tay, Wee Shan
    Li, Yongxin
    Yang, Xiang-Yuan
    Pullarkat, Sumod A.
    Leung, Pak-Hing
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2020, 914
  • [50] A water soluble and air-stable tripalladium cluster
    Yang, Fu-Ming
    Chen, Po-Yuan
    Lee, Chun-Chin
    Liu, Yi-Hung
    Peng, Shie-Ming
    Chou, Pi-Tai
    Liu, Shiuh-Tzung
    DALTON TRANSACTIONS, 2012, 41 (19) : 5782 - 5784