Reduction of Aromatic Dimethyl Ene-Dicarboxylates to Dimethyl Succinates with Titanium Ylides

Title:Reduction of Aromatic Dimethyl Ene-Dicarboxylates to Dimethyl Succinates with Titanium Ylides

Volume: 10 Issue: 2

Author(s): Reza-Ali Fallahpour*

Affiliation:

• Department of Chemistry and Biochemistry, University of Bern, Freistrasse 3, CH- 3012 Bern,Switzerland

Keywords: Tebbe- and Takai-reagents, methenylation, double bonds, reagents, aromatic, isomerisation.

Abstract:

Background: Generally, it was assumed that Tebbe- and Takai-reagents are useful for methenylation reactions.

Objective: Applying these reagents to aromatic ene dicarboxylates, unexpectedly the reduction of double bonds was achieved. There is, however, a different behaviour of both reagents. Takai-reagent yields reduction while Tebbe-reagent prefers isomerisation.

Methods: A selective and unique method has been shown to reduce a double bond of ene-dicarboxylates while both carboxylic groups are not affected at all. In addition, this method is easy and very cheap using Takai-reagent.

Results: If isomerisation is to be carried out, without any reduction of a double bond, Tebbe-reagent can be applied. To our knowledge, such reactions have not been published yet.

Conclusion: We have shown a selective methodology to reduce aromatic ene-dicarboxylates with titanium ylides.

Cite this article as:

Fallahpour Reza-Ali *, Reduction of Aromatic Dimethyl Ene-Dicarboxylates to Dimethyl Succinates with Titanium Ylides, Current Catalysis 2021; 10 (2) . https://dx.doi.org/10.2174/2211544710666210317160132