RING-OPENING METATHESIS

Ring Opening Metathesis (Polymerization) - ROM(P)

Strained rings may be opened by a ruthenium carbene-catalyzed reaction with a second alkene following the mechanism of the Cross Metathesis. The driving force is the relief of ring strain. As the products contain terminal vinyl groups, further reactions of the Cross Metathesis variety may occur. Therefore, the reaction conditions (time, concentrations,...) must be optimized to favor the desired product.

Strain rings may be opened by a ruthenium carbene-catalyzed reaction with a second alkene  following the mechanisms of the Cross Metathesis. Driving force is the relief of ring strain. As the products contain terminal vinyl groups, further reactions of the Cross Metathesis variety may occur. Therefore, the reaction conditions (time, concentrations,...) must be optimized to favor the desired product.

In absence of excess of a second reaction partner, polymerization occurs (ROMP):

The reverse reaction - the Ring Closing Metathesis - is a valuable synthesis tool for preparing from 5- up to 30-membered rings.

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Mechanism of Ring Opening Metathesis

Recent Literature

ROMPgel-Supported Triphenylphosphine with Potential Application in Parallel Synthesis

Comparison of Ru- and Mo-Based Chiral Olefin Metathesis Catalysts. Complementarity in Asymmetric Ring-Opening/Cross-Metathesis Reactions of Oxa- and Azabicycles