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

Author(s):

Reza-Ali Fallahpour*  

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 in both reagents. Takai-reagent yields reduction while Tebbe- reagent prefers isomerisation.

Methods: It shows a selective and unique method 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 interested in just isomerisation, without any reduction of double bond, Tebbe-reagent can be applied. Due to our knowledge, such reactions were not published yet.

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

Keywords:

Tebbe- and Takai-reagents, methenylation, double bonds, reagents, aromatic, isomerisation

Affiliation:

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



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