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Issue 14, 2011
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Synthesis and characterization of bis-cyclopropanated 1,3,5-tricarbonyl compounds. A combined synthetic, spectroscopic and theoretical study

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Abstract

Bis-cyclopropanated 1,3,5-tricarbonyl compounds were prepared by a sequence of Claisen condensations and cyclopropanations. The optimization of the conditions proved to be very important to suppress retro-Claisen reactions. The conformation of these molecules was studied by experimental and computational methods. The syn/syn;syn/syn conformation is present for all derivatives. It is exclusively present in the case of the derivative containing a phenyl group located at the terminal carbon atom. In most cases, equilibria with other conformers are found.

Graphical abstract: Synthesis and characterization of bis-cyclopropanated 1,3,5-tricarbonyl compounds. A combined synthetic, spectroscopic and theoretical study

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Article information


Submitted
22 Mar 2011
Accepted
26 Apr 2011
First published
26 Apr 2011

Org. Biomol. Chem., 2011,9, 5172-5184
Article type
Paper

Synthesis and characterization of bis-cyclopropanated 1,3,5-tricarbonyl compounds. A combined synthetic, spectroscopic and theoretical study

T. Rahn, F. Bendrath, M. Hein, W. Baumann, H. Jiao, A. Börner, A. Villinger and P. Langer, Org. Biomol. Chem., 2011, 9, 5172
DOI: 10.1039/C1OB05455D

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