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

Organic & Biomolecular Chemistry Pub Date: 2011-04-26 DOI: 10.1039/C1OB05455D

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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