1,3-bis(N,N-dialkylamino)imidazolin-2-ylidenes:: Synthesis and reactivity of a new family of stable N-heterocyclic carbenes

被引：62
|
作者：
Alcarazo, M
Roseblade, SJ
Alonso, E
Fernández, R
Alvarez, E
Lahoz, FJ
Lassaletta, JM
机构：
[1] US, CSIC, Inst Invest Quim, E-41092 Seville, Spain
[2] Univ Seville, Dept Quim Organ, E-41012 Seville, Spain
[3] CSIC, Inst Ciencia Mat Aragon, E-50009 Zaragoza, Spain
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 41期
关键词：
D O I：
10.1021/ja0471119
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis of stable 1,3-bis(N,N-dialkylamino)imidazolin-2-ylidenes was accomplished from readily available chiral bis-hydrazones after reduction or addition of PhMgCl, cyclization to imidazolinium salts, and treatment with KN(SiMe3)2. This strategy allows the obtention of free imidazolin-2-ylidenes and their Rh(COD)Cl complexes in enantiomerically pure form. The σ-donor ability of dialkylamino-substituted diaminocarbenes was found to be slightly higher than that of alkyl(aryl) analogues. Copyright © 2004 American Chemical Society.
引用
收藏
页码：13242 / 13243
页数：2
相关论文
共 50 条
  • [21] Synthesis and Reactivity of Three New N-Heterocyclic Silylenes
    Tomasik, Adam C.
    Mitra, Amitabha
    West, Robert
    ORGANOMETALLICS, 2009, 28 (01) : 378 - 381
  • [22] Synthesis and Structures of Copper(I) Complexes with Phosphino-Functionalized N-Heterocyclic Carbenes (NHCP) and Bis-N-Heterocyclic Carbenes (Bis-NHC)
    Kuehnel, Erik
    Shishkov, Igor V.
    Rominger, Frank
    Oeser, Thomas
    Hofmann, Peter
    ORGANOMETALLICS, 2012, 31 (22) : 8000 - 8011
  • [23] Free radical polymerization of 2-[(N,N-dialkylamino)methyl]-1,3-butadienes
    Wu, Lifen
    Mohanty, A.K.
    Sheares, Valerie V.
    American Chemical Society, Polymer Preprints, Division of Polymer Chemistry, 2000, 41 (01): : 97 - 98
  • [24] 1,2,4-Triazol-3-ylidenes with an N-2,4-Dinitrophenyl Substituent as Strongly π-Accepting N-Heterocyclic Carbenes
    Sato, Tetsuo
    Hirose, Yoichi
    Yoshioka, Daisuke
    Shimojo, Tsubasa
    Oi, Shuichi
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (46) : 15710 - 15718
  • [25] N-phosphanyl-imidazolin-2-ylidenes: Novel stable carbenes as bidentate ligands for late transition metals
    Marchenko, Anatoliy
    Koidan, Heorgyi
    Hurieva, Anastasiya
    Kurpiieva, Oleha
    Vlasenko, Yurii
    Kostyuk, Aleksandr
    Tubaro, Cristina
    Lenarda, Anna
    Biffis, Andrea
    Graiff, Claudia
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2014, 771 : 14 - 23
  • [26] Synthesis of 2,5-bis(N,N-dialkylamino)thiophenes or 1-alkyl-2-N,N-dialkylamino-5-methylthiop yrroles from propargylic amines and isothiocyanates
    Tetrahedron Lett, 41 (7241):
  • [27] Synthesis, Reactivity and Electronic Properties of Quinazolin-2-one-Based N-Heterocyclic Carbenes
    Brueggemann, Peter
    Mzyk, Karol
    Molter, Marius
    Nellesen, Joscha
    Schaper, Klaus
    Ganter, Christian
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2022, 2022 (02)
  • [28] New cerberus-type N-heterocyclic carbenes: Synthesis and coordination
    Hooper, Reagan
    Malone, John
    Tapu, Daniela
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [29] Thiazetidin-2-ylidenes as four membered N-heterocyclic carbenes: theoretical studies and the generation of complexes with N+ center
    Dubey, Gurudutt
    Mahawar, Nutan
    Singh, Tejender
    Saha, Nirjhar
    Sahoo, Subash C.
    Bharatam, Prasad, V
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2022, 24 (02) : 629 - 633
  • [30] Synthesis and UV/Vis spectroscopic properties of new [2-(N,N-dialkylamino)-1,3-dithiolium-4-yl]phenolates
    Birsa, ML
    Ganju, D
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2003, 16 (04) : 207 - 212
12345