Issue 26, 2006
From the journal:

Chemical Communications

Pummerer fragmentation vs.Pummerer rearrangement: a mechanistic analysis†

Benoît Laleu,a   Marco Santarem Machadoa  and  Jérôme Lacour*a  

* Corresponding authors

a Department of Organic Chemistry, University of Geneva, Quai E. Ansermet 30, Switzerland
E-mail: jerome.lacour@chiorg.unige.ch

Abstract

Depending upon the nature of the substituent at the β-position of the sulfoxide moiety, a Pummerer reaction can be oriented “at will” towards Cα–H (rearrangement) or Cα–Cβ (fragmentation) bond cleavage.

Graphical abstract: Pummerer fragmentation vs. Pummerer rearrangement: a mechanistic analysis

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Article information

DOI
https://doi.org/10.1039/B605187A
Article type
Communication
Submitted
11 Apr 2006
Accepted
05 May 2006
First published
25 May 2006

Chem. Commun., 2006, 2786-2788

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Pummerer fragmentation vs. Pummerer rearrangement: a mechanistic analysis

B. Laleu, M. S. Machado and J. Lacour, Chem. Commun., 2006, 2786 DOI: 10.1039/B605187A

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