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Synthesis 2013; 45(18): 2485-2498
DOI: 10.1055/s-0033-1338516
DOI: 10.1055/s-0033-1338516
review
Aminocyclopropenium Ions: Synthesis, Properties, and Applications
Further Information
Publication History
Received: 22 May 2013
Accepted after revision: 20 June 2013
Publication Date:
29 August 2013 (online)
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Abstract
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.
1 Introduction
2 Preparation
3 Properties
3.1 Stability
3.2 Redox Behavior
3.3 Ion Pair Strain
4 Reactions
5 Applications
5.1 Ionic Liquids
5.2 Metal Complexes
5.2.1 TDAC π-Complexes
5.2.2 BDAC σ-Complexes
5.2.3 Cyclopropenimine Ligands
5.2.4 BDAC–Phosphorus Ligands
5.3 Brønsted Bases
6 Conclusion
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For selected reviews, see:
For reviews of cyclopropene chemistry, see:
For reviews on NHC ligands, see:
For additions to non-metals, see:
For additions to metals, see:
During the preparation of this manuscript Alcarazo and co-workers reported the synthesis and characterization of cyclopropenylidene-stabilized N-, S-, Se-, and Te-centered cations:
For examples of the synthesis of cyclopropenimines, see: