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Vol. 28 No. 5 (2016): Vol 28 Issue 5

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o-Eugenol: A Versatile Molecule for Production of Polyfunctional Alkenes via Organometallic Catalysis

https://doi.org/10.14233/ajchem.2016.19554
Abdullah Sulaiman Al-Ayed
Chemistry Department, College of Science and Arts, Al-Rass, P.O. Box 53, Qassim University, Buraidah 51477, Saudi Arabia
Naceur Hamdi
Chemistry Department, College of Science and Arts, Al-Rass, P.O. Box 53, Qassim University, Buraidah 51477, Saudi Arabia; Higher Institute of Environmental Science and Technologies (HIEST-Borj Cedria, Tunisia), University of Carthage, Touristic Road of Soliman, BP 95, Hammam-Lif 2050, Tunisia
Maurizio Peruzzini
Istituto di Chimica dei Composti Organo Metallici, Via Madonna del Piano, 10 Area di Ricerca del CNR, Building C, Polo Scientifico di Sesto Fiorentino, 50019 Sesto Fiorentino (FI), Italy

Corresponding Author(s) : Naceur Hamdi

naceur.hamdi@isste.rnu.tn

Asian Journal of Chemistry, Vol. 28 No. 5 (2016): Vol 28 Issue 5

Abstract

In this study, the synthesis and cross metathesis of o-eugenol (2-allyl-6-methoxy phenol) has been investigated. Synthesis was conducted through two stages of reaction. The first step in the synthetic procedure was to obtain the intermediate 1-but-3-enyl-2-methoxy benzene. Then the heating of the obtained intermediate will initiate will initiate a [3,3] sigmatropic rearrangement to give the o-eugenol with a good yield. The ruthenium-catalyzed cross-metathesis of o-eugenol derivatives with electron deficient olefins including methyl acrylate, acrylonitrile and acrylamides was also reported. In addition the polymerization of 1-allyl-2-(allyloxy)-3-methoxybenzene was possible by acyclic diene metathesis and this allowed to synthesize a polymer from a natural substrate. All the resulting structures were supported by the spectroscopic data.

Keywords

Claisen rearrangement o-Eugenol Isomerization O-Allylation Benzoquinone Cetyltrimethylammonium bromide
Al-Ayed, A. S., Hamdi, N., & Peruzzini, M. (2016). o-Eugenol: A Versatile Molecule for Production of Polyfunctional Alkenes via Organometallic Catalysis. Asian Journal of Chemistry, 28(5), 960–964. https://doi.org/10.14233/ajchem.2016.19554
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