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DOI: 10.1055/s-0034-1378393
Rearrangements of Nitrile-Stabilized Ammonium Ylides
Publication History
Received: 23 April 2014
Accepted after revision: 13 June 2014
Publication Date:
18 July 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201418/lookinside/thumbnails/10.1055-s-0034-1378393-1.jpg)
Dedicated to Professor Paul Margaretha on the occasion of his 70th birthday
Abstract
Rearrangements of nitrile-stabilized ammonium ylides are useful reactions for the construction of alkylamines, nitrogen heterocycles, or carbonyl compounds. In spite of their attractive synthetic potential, they are much less frequently used than rearrangements of ammonium ylides either carrying charge-stabilizing carbonyl groups or being devoid of additional stabilization of the negative charge. This review focuses on different classes of rearrangements of nitrile-stabilized ammonium ylides as well as their application in synthetic organic chemistry.
1 Introduction
2 [1,2]-Stevens Rearrangements
3 [2,3]-Sommelet–Hauser Rearrangement
4 [2,3]-Stevens Rearrangements
5 Competitive [1,2]-, [2,3]-, and [1,4]-Rearrangements
6 [1,4]-Rearrangements Involving Ring Expansion
7 Summary
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