Issue 3, 2008
From the journal:

Organic & Biomolecular Chemistry

Dichotomies in microwave-assisted propargyl-isomerization–Claisen domino sequences dependent on base strengths†‡

Daniel M. D'Souza,a   Wei-Wei Liao,a   Frank Romingera  and  Thomas J. J. Müller*ab  

* Corresponding authors

a Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69121 Heidelberg, Germany

b Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany
E-mail: ThomasJJ.Mueller@uni-duesseldorf.de
Fax: +221 81 12298
Tel: +221 81 14324

Abstract

Microwave-assisted unimolecular isomerization–Claisen domino reactions of 1,3-di(hetero)aryl propargyl trityl ethers lead, depending on the basicity of the amine, either to the formation of tricyclo[3.2.1.02,7]oct-3-enes (with triethylamine) or to indanes (with DBU). Based upon product analyses and computations, this base dependent dichotomy can be rationalized as a sequel of pericyclic reactions with intermediate protonation and deprotonation.

Graphical abstract: Dichotomies in microwave-assisted propargyl-isomerization–Claisen domino sequences dependent on base strengths

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Article information

DOI
https://doi.org/10.1039/B714351F
Article type
Paper
Submitted
17 Sep 2007
Accepted
26 Nov 2007
First published
17 Dec 2007

Org. Biomol. Chem., 2008,6, 532-539

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Dichotomies in microwave-assisted propargyl-isomerization–Claisen domino sequences dependent on base strengths

D. M. D'Souza, W. Liao, F. Rominger and T. J. J. Müller, Org. Biomol. Chem., 2008, 6, 532 DOI: 10.1039/B714351F

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