Aminocyclopropenium Ions: Synthesis, Properties, and Applications

被引：82

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 [J].

BADRI, M ;

BRUNET, JJ .

TETRAHEDRON LETTERS, 1992, 33 (31) :4435-4438

[2] Cyclopropenimine-Catalyzed Enantioselective Mannich Reactions of tert-Butyl Glycinates with N-Boc-Imines [J].

Bandar, Jeffrey S. ;

Lambert, Tristan H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) :11799-11802

[3] Enantioselective Bronsted Base Catalysis with Chiral Cyclopropenimines [J].

Bandar, Jeffrey S. ;

Lambert, Tristan H. .

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 [J].

Baric, D ;

Maksic, ZB .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2003, 16 (10) :753-763

[5] DIPHENYLCYCLOPROPENONE [J].

BRESLOW, R ;

EICHER, T ;

KREBS, A ;

PETERSON, RA ;

POSNER, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1320-&

[6] SYNTHESIS OF THE S-TRIPHENYLCYCLOPROPENYL CATION [J].

BRESLOW, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (19) :5318-5318

[7] Synthesis and Coordination Properties of Nitrogen(I)-Based Ligands [J].

Bruns, Hans ;

Patil, Mahendra ;

Carreras, Javier ;

Vazquez, Arcadio ;

Thiel, Walter ;

Goddard, Richard ;

Alcarazo, Manuel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (21) :3680-3683

[8] Structure of a discrete dichloride hexahydrate cube as a tris(diisopropylamino)cyclopropenium salt [J].

Butchard, James R. ;

Curnow, Owen J. ;

Garrett, David J. ;

Maclagan, Robert G. A. R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) :7550-7553

[9] Structural, theoretical and spectroscopic studies of the dichloride hexahydrate cube [Cl2(H2O)6]2- [J].

Butchard, James R. ;

Curnow, Owen J. ;

Garrett, David J. ;

Maclagan, Robert G. A. R. ;

Libowitzky, Eugen ;

Piccoli, Paula M. B. ;

Schultz, Arthur 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 [J].

Carreras, Javier ;

Patil, Mahendra ;

Thiel, Walter ;

Alcarazo, Manuel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (40) :16753-16758

← 1 2 3 4 5 6 7 8 9 →