Synthesis 2013; 45(18): 2485-2498
DOI: 10.1055/s-0033-1338516
review
© Georg Thieme Verlag Stuttgart · New York

Aminocyclopropenium Ions: Synthesis, Properties, and Applications

Jeffrey S. Bandar
Columbia University, Department of Chemistry, 3000 Broadway, New York, NY 10027, USA   Fax: +1(212)9321289   Email: tl2240@columbia.edu
,
Tristan H. Lambert*
Columbia University, Department of Chemistry, 3000 Broadway, New York, NY 10027, USA   Fax: +1(212)9321289   Email: tl2240@columbia.edu
› Author Affiliations
Further Information

Publication History

Received: 22 May 2013

Accepted after revision: 20 June 2013

Publication Date:
29 August 2013 (eFirst)

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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