Open Chemistry Journal

ISSN: 1874-8422 ― Volume 6, 2019

A New Synthetic Method of 1,5-Dimethyl-3-Oxabicyclo[3.1.0] Hexane-2,4-Dione

Youcef Mechehoud1, Nadjah Belattar1, *, Samir Benayache1, Fadila Benayache1, Paul Mosset2
1 Research Unity of Valorization of Natural Resources, Bioactive Molecules and Physicochemical Biological Analysis, Department of Chemistry, Faculty of Exact Sciences, University of Mentouri- Brothers, Constantine-1, 25000, Algeria.
2 University of Rennes, 1263 Avenue of General Leclerc, Building 10 A, Door 154/1, 35042 Rennes Cedex, France



We have described in this reported work a new method in the synthesis of cis-1,5-dimethyl -3-oxabicyclo [3.1.0] hexane-2,4-dione in good yield.


Optimization of practical conditions leads to obtain 1,3-cyclopropanedicarboxylic anhydrides as important precursors of functionalized cyclopropane derivatives.


The condensation of 2-chloropropanoic acid with ethyl methacrylate using (2M) LDA dissolved in hexane and THF at (-80°C), and the treatment with acetyl chloride permit to obtain the substituted 1,3- cyclopropanedicarboxylic anhydride .


We have proceeded to the synthesis of cis-1,5-dimethyl -3-oxabicyclo [3.1.0] hexane-2,4-dione as functionalized organic compound with high efficiency ,taking into account the regioselectivity of carbanion attack to double bond activated by an electrophilic group.


Using (2M) LDA dissolved in hexane and THF at (-80°C) is a good way to afford the enantioselective substituted 1,3- cyclopropanedicarboxylic anhydrides.

Keywords: Cis-3-oxabicyclo, LDA, Cyclopropanedicarboxylic anhydrides, Condensation, Regioselectivity, Electrophilic.

Article Information

Identifiers and Pagination:

Year: 2018
Volume: 5
First Page: 44
Last Page: 50
Publisher Id: CHEM-5-44
DOI: 10.2174/1874842201805010044

Article History:

Received Date: 09/03/2018
Revision Received Date: 10/05/2018
Acceptance Date: 31/05/2018
Electronic publication date: 29/06/2018
Collection year: 2018

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© 2018 Mechehoud et al.

open-access license: This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 International Public License (CC-BY 4.0), a copy of which is available at: This license permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

* Address correspondence to this author at the Research Unity of Valorization of Natural Resources, Bioactive Molecules and Physicochemical Biological Analysis, Department of Chemistry, Faculty of Exact Sciences, University of Mentouri- Brothers, Constantine-1, Algeria; E-mail:


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