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

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 05期

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

页码：595 / 598

页数：4

共 50 条

[21] Air-stable manganese (III)
West, Thomas
NATURE SYNTHESIS, 2022, 1 (10): : 750 - 750
[22] Spontaneous Formation of an Air-Stable Radical upon the Direct Fusion of Diphenylmethane to a Triarylporphyrin
Kato, Kenichi
Cha, Wonhee
Oh, Juwon
Furukawa, Ko
Yorimitsu, Hideki
Kim, Dongho
Osuka, Atsuhiro
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (30) : 8711 - 8714
[23] C4 Cumulene and the Corresponding Air-Stable Radical Cation and Dication
Li, Yan
Mondal, Kartik Chandra
Samuel, Prinson P.
Zhu, Hongping
Orben, Claudia M.
Panneerselvam, Saravanan
Dittrich, Birger
Schwederski, Brigitte
Kaim, Wolfgang
Mondal, Totan
Koley, Debasis
Roesky, Herbert W.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (16) : 4168 - 4172
[24] An air-stable N-heterocyclic carbene iminoxyl borate radical zwitterion
Kim, Youngsuk
Lee, Eunsung
CHEMICAL COMMUNICATIONS, 2018, 54 (50) : 6824 - 6827
[25] An Azulene-Based Chiral Helicene and Its Air-Stable Cation Radical
Narita, Masahiro
Teraoka, Takaaki
Murafuji, Toshihiro
Shiota, Yoshihito
Yoshizawa, Kazunari
Mori, Shigeki
Uno, Hidemitsu
Kanegawa, Shinji
Sato, Osamu
Goto, Kenta
Tani, Fumito
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2019, 92 (11) : 1867 - 1873
[26] An Amphoteric Switch to Aromatic and Antiaromatic States of a Neutral Air-Stable 25π Radical
Gopalakrishna, Tullimilli Y.
Reddy, J. Sreedhar
Anand, Venkataramanarao G.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (41) : 10984 - 10987
[27] Synthesis and structure of an air-stable, free-radical cobalt(III) semiquinone complex
Arzberger, S
Soper, J
Anderson, OP
la Cour, A
Wicholas, M
INORGANIC CHEMISTRY, 1999, 38 (04) : 757 - 761
[28] Air-stable palladium catalytic systems
不详
CHEMICAL & ENGINEERING NEWS, 1999, 77 (38) : 44 - 44
[29] Air-stable chiral primary phosphines
Hiney, Rachel M.
Higham, Lee J.
Gilheany, Declan G.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[30] Dabbling with air-stable organoaluminum species
Biswas, K
Chapron, A
Cooper, T
Fraser, PK
Novak, A
Prieto, O
Woodward, S
PURE AND APPLIED CHEMISTRY, 2006, 78 (02) : 511 - 518

← 1 2 3 4 5 →