Article | REF: AF6232 V1

Metathesis: from polymerization to the synthesis of complex molecules

Authors: Janine COSSY, Claude COMMANDEUR, Malgorzata COMMANDEUR

Publication date: July 10, 2012

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ABSTRACT

The first observed metathesis was the transformation of a cyclic olefine into an unsaturated polymer in the presence of a metallic catalyst. The major interest of this reaction was understood only later on the occasion of obtaining an unsaturated polymer with a high mass and double bonds, after having left a cyclic olefine in teh presence of metals such as tungstene or molybdene. N. Calderon, a chemist from the Good Year Tire, then showed that these phenomena of polymerization and/or transformation of olefines into other olefines were caused by a phenomenon he called "metathesis". The metathesis reaction was then extended to the ene-ynes and alkynes thus enabling organic chemists to have an easy access to complex molecules.

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AUTHORS

  • Janine COSSY: Professor - Director, Organic Chemistry Laboratory, ESPCI Paris Tech, CNRS (UMR 7084)

  • Claude COMMANDEUR: Doctor - Postdoctoral researcher at the Organic Chemistry Laboratory, ESPCI Paris Tech, CNRS (UMR 7084)

  • Malgorzata COMMANDEUR: Doctor - Postdoctoral researcher at the Organic Chemistry Laboratory, ESPCI Paris Tech, CNRS (UMR 7084)

 INTRODUCTION

Olefin metathesis is a reaction that was first observed in the 1950s by a DuPont petrochemist, H.S. Eleuterio . This chemist had observed the transformation of a cyclic olefin into an unsaturated polymer in the presence of a metal catalyst, but had not realized the importance of this reaction. By contrast, in 1964, R.L. Banks and G.C. Bailey of Phillips Petroleum saw the impact that olefin metathesis could have, as they had been able to transform propylene into ethylene and butene by heating, thanks to the presence of a molybdenum catalyst . In the same year, G. Natta, who belonged to the Milan Industrial Research Institute, had found that by leaving a cyclic olefin in the presence of metals such as tungsten or molybdenum, he could obtain a high-mass unsaturated polymer with double bonds and, in 1967, N. Calderon, a chemist at Good Year Tire, showed that these polymerizations and/or transformations of olefins into other olefins were due to a phenomenon he called "metathesis" . In Greek, "meta" means change and "thesis" means position. It has to be said that, in the 1960s, the mechanism of metathesis was much debated and, at that time, far from elucidated. It wasn't until 1971, inspired by the work of Natta, Banks, Bailey and Fischer, who had identified a metal-carbon, that Y. Chauvin and J.L. Hérisson proposed a mechanism involving a metal-carbon that could act as a catalyst in the metathesis reaction between two alkenes. Avant-garde, Y. Chauvin and J.L....

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Metathesis: from polymerization to the synthesis of complex molecules