Aminocyclopropenium Ions: Synthesis, Properties, and Applications

被引：80
作者：
Bandar, Jeffrey S. [1 ]
Lambert, Tristan H. [1 ]
机构：
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
来源：
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 18期
关键词：
cyclopropenium ions; aromaticity; cyclopropenimines; ionic liquids; ligands; TRANSITION-METAL-COMPLEXES; CYCLOPROPENYL CATIONS; ELECTRONIC-STRUCTURE; DRIVING-FORCE; DELTIC ACID; PAIR STRAIN; IODIDE-IONS; SYSTEMS; CATALYSIS; LIQUIDS;
D O I：
10.1055/s-0033-1338516
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This review covers the preparation, physical properties, and applications of cyclopropenium ions bearing one, two, or three amino substituents. It provides a description of the most reliable methods to access these unique structures as well as a discussion of the reactivity profiles of the common subtypes. 1Introduction 2Preparation 3Properties 3.1Stability 3.2Redox Behavior 3.3Ion Pair Strain 4Reactions 5Applications 5.1Ionic Liquids 5.2Metal Complexes 5.2.1TDAC -Complexes 5.2.2BDAC sigma-Complexes 5.2.3Cyclopropenimine Ligands 5.2.4BDAC-Phosphorus Ligands 5.3BrOnsted Bases 6Conclusion
引用
收藏
页码：2485 / 2498
页数：14
相关论文
共 88 条
  • [1] IONIC LIQUIDS AS SOLVENTS FOR THE REGIOSELECTIVE O-ALKYLATION OF C/O AMBIDENT NUCLEOPHILES
    BADRI, M
    BRUNET, JJ
    [J]. TETRAHEDRON LETTERS, 1992, 33 (31) : 4435 - 4438
  • [2] Cyclopropenimine-Catalyzed Enantioselective Mannich Reactions of tert-Butyl Glycinates with N-Boc-Imines
    Bandar, Jeffrey S.
    Lambert, Tristan H.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) : 11799 - 11802
  • [3] Enantioselective Bronsted Base Catalysis with Chiral Cyclopropenimines
    Bandar, Jeffrey S.
    Lambert, Tristan H.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (12) : 5552 - 5555
  • [4] Non-additivity of the static correlation energy of π-electrons in planar molecules as a manifestation of anti/aromaticity
    Baric, D
    Maksic, ZB
    [J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2003, 16 (10) : 753 - 763
  • [5] DIPHENYLCYCLOPROPENONE
    BRESLOW, R
    EICHER, T
    KREBS, A
    PETERSON, RA
    POSNER, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) : 1320 - &
  • [6] SYNTHESIS OF THE S-TRIPHENYLCYCLOPROPENYL CATION
    BRESLOW, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (19) : 5318 - 5318
  • [7] Synthesis and Coordination Properties of Nitrogen(I)-Based Ligands
    Bruns, Hans
    Patil, Mahendra
    Carreras, Javier
    Vazquez, Arcadio
    Thiel, Walter
    Goddard, Richard
    Alcarazo, Manuel
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (21) : 3680 - 3683
  • [8] Structure of a discrete dichloride hexahydrate cube as a tris(diisopropylamino)cyclopropenium salt
    Butchard, James R.
    Curnow, Owen J.
    Garrett, David J.
    Maclagan, Robert G. A. R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) : 7550 - 7553
  • [9] Structural, theoretical and spectroscopic studies of the dichloride hexahydrate cube [Cl2(H2O)6]2-
    Butchard, James R.
    Curnow, Owen J.
    Garrett, David J.
    Maclagan, Robert G. A. R.
    Libowitzky, Eugen
    Piccoli, Paula M. B.
    Schultz, Arthur J.
    [J]. DALTON TRANSACTIONS, 2012, 41 (38) : 11765 - 11775
  • [10] Exploiting the π-Acceptor Properties of Carbene-Stabilized Phosphorus Centered Trications [L3P] 3+: Applications in Pt(II) Catalysis
    Carreras, Javier
    Patil, Mahendra
    Thiel, Walter
    Alcarazo, Manuel
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (40) : 16753 - 16758
123456789