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Current Catalysis

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ISSN (Print): 2211-5447
ISSN (Online): 2211-5455

Research Article

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

Author(s): Reza-Ali Fallahpour*

Volume 10 , Issue 2 , 2021

Published on: 17 March, 2021

Page: [140 - 145] Pages: 6

DOI: 10.2174/2211544710666210317160132

Price: $65

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.

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

Graphical Abstract

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