Issue 17, 2008
From the journal:

Organic & Biomolecular Chemistry

Synthesis and solution structure of 3,5-dioxopimelic acid diesters—stable 1,3,5,7-tetracarbonyl derivatives

Stefanie Reim,a   Dirk Michalik,*ab   Klaus Weisz,c   Zhou Xiaoc  and  Peter Langer*ab  

* Corresponding authors

a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, Germany
E-mail: peter.langer@uni-rostock.de
Fax: 00 49 381 49864112
Tel: 0049 381 4986410

b Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, Germany
E-mail: dirk.michalik@catalysis.de
Tel: 0049 381 4986353

c Institut für Biochemie, Ernst-Moritz-Arndt-Universität Greifswald, Felix-Hausdorff-Str. 4, Germany

Abstract

A variety of 3,5-dioxopimelic acid diesters, stable 1,3,5,7-tetracarbonyl derivatives, were prepared by catalytic condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with methyl malonyl chloride. The keto–enol tautomerization of these compounds has been investigated by NMR spectroscopy. One keto and up to four enolic tautomers could be detected in chloroform solution and the influence of the substituents on the tautomeric equilibria has been studied.

Graphical abstract: Synthesis and solution structure of 3,5-dioxopimelic acid diesters—stable 1,3,5,7-tetracarbonyl derivatives

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Article information

DOI
https://doi.org/10.1039/B805808C
Article type
Paper
Submitted
07 Apr 2008
Accepted
29 May 2008
First published
30 Jun 2008

Org. Biomol. Chem., 2008,6, 3079-3084

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Synthesis and solution structure of 3,5-dioxopimelic acid diesters—stable 1,3,5,7-tetracarbonyl derivatives

S. Reim, D. Michalik, K. Weisz, Z. Xiao and P. Langer, Org. Biomol. Chem., 2008, 6, 3079 DOI: 10.1039/B805808C

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