California Institute of Technology

Hyunjin M Kim

Robert H Grubbs

Choon Woo Lee

Tae-Lim Choi

Oren A Scherman

This invention relates generally to synthetic procedures that include the step of ring-opening metathesis of cyclic olefins and reaction with an acyclic diene co-reactant to produce olefin macrocycles by ring expansion, or alternatively. The ring expansion of the cyclic olefin is provided by three types of sequential olefin metathesis (ring-opening, cross, and ring-closing olefin metathesis). More particularly, the invention pertains to synthesis of olefin macrocycles via olefin metathesis reactions using a Group 8 transition metal complex as the metathesis catalyst. Macrocycles provided herein have a variety of uses in the pharmaceutical, biomedical, organic synthesis and chemical industries, such as the production of crown ethers that are useful as metal complexing species.

Ring-expansion of cyclic olefins metathesis reactions with an acyclic diene

A method is provided for synthesizing a polymer in a controlled fashion using a ring-opening metathesis polymerization (ROMP) reaction, wherein polymerization is carried out using a catalytically effective amount of an olefin metathesis catalyst and a bridged bicyclic or polycyclic olefin monomer that contains at least two heteroatoms directly or indirectly linked to each other. Preferred catalysts are Group 8 transition metal complexes, particularly complexes of Ru and Os. Such complexes include the ruthenium bisphosphine complex (PCy)(Cl)Ru&#x2550;CHPh (1) and the ruthenium carbene complex (IMesH)(PCy)(Cl)Ru&#x2550;CHPh (2). The invention also provides novel regioregular polymers synthesized using the aforementioned methodology, wherein the polymers may be saturated, unsaturated, protected, and/or telechelic. An exemplary polymer is poly((vinyl alcohol)-alt-methylene)(MVOH).

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San Ramon, CA, United States of America

Hyunjin M Kim