Rearrangements of Nitrile-Stabilized Ammonium Ylides

Günther Lahm; Julio Cesar Orejarena Pacheco; Till Opatz

doi:10.1055/s-0034-1378393

Synthesis, Table of Contents

Synthesis 2014; 46(18): 2413-2421
DOI: 10.1055/s-0034-1378393

short review

Rearrangements of Nitrile-Stabilized Ammonium Ylides

Günther Lahm

Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10–14, 55128 Mainz, Germany Fax: +49(6131)3922338 Email: opatz@uni-mainz.de

,

Julio Cesar Orejarena Pacheco

Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10–14, 55128 Mainz, Germany Fax: +49(6131)3922338 Email: opatz@uni-mainz.de

,

Till Opatz*

Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10–14, 55128 Mainz, Germany Fax: +49(6131)3922338 Email: opatz@uni-mainz.de

› Author Affiliations

Abstract

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Dedicated to Professor Paul Margaretha on the occasion of his 70^th 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

Key words

ylides - rearrangement - ring expansion - amines - heterocycles

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References

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