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
[51]   Stable Cyclic Carbenes and Related Species beyond Diaminocarbenes [J].
Melaimi, Mohand ;
Soleilhavoup, Michele ;
Bertrand, Guy .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (47) :8810-8849
[52]   CATALYSIS OF CYCLOPROPENYLIDENE PALLADIUM(II) COMPLEXES FOR THE ISOMERIZATION OF QUADRICYCLANE TO NORBORNADIENE [J].
MIKI, S ;
OHNO, T ;
IWASAKI, H ;
MAEDA, Y ;
YOSHIDA, Z .
TETRAHEDRON, 1988, 44 (01) :55-60
[53]   SYNTHESES, SPECTROSCOPIC CHARACTERIZATION AND ELECTRONIC-STRUCTURE OF CYCLOPROPENYLIDENE LIGATED PLATINUM COMPLEXES [J].
MIKI, S ;
OHNO, T ;
IWASAKI, H ;
YOSHIDA, ZI .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1988, 1 (06) :333-349
[54]  
Nolan S P., 2006, N HETEROCYCLIC CARBE
[55]  
PAQUETTE LA, 1967, TETRAHEDRON LETT, P5039
[56]   Synthesis, Structure, and Reactivity of Carbene-Stabilized Phosphorus(III)-Centered Trications [L3P]3+ [J].
Petuskova, Jekaterina ;
Patil, Mahendra ;
Holle, Sigrid ;
Lehmann, Christian W. ;
Thiel, Walter ;
Alcarazo, Manuel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (51) :20758-20760
[57]   Cyclopropenylylidene-Stabilized Diaryl and Dialkyl Phosphenium Cations: Applications in Homogeneous Gold Catalysis [J].
Petuskova, Jekaterina ;
Bruns, Hans ;
Alcarazo, Manuel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (16) :3799-3802
[58]   REACTION OF N-(PARA-TOLYLSULFONYL)DIPHENYLCYCLOPROPENIMINE WITH PYRIDINIUM AND ISOQUINOLINIUM YLIDES [J].
PILLI, RA ;
RODRIGUES, JAR ;
KASCHERES, A .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :1084-1091
[59]   Applications of ionic liquids in the chemical industry [J].
Plechkova, Natalia V. ;
Seddon, Kenneth R. .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (01) :123-150
[60]  
Reutiv O.A., 1977, Russ. Chem. Rev, V46, P1040