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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Published on: December 16, 2022

Simple, chemoselective, catalytic olefin isomerization.

Steven W M Crossley¹, Francis Barabé, Ryan A Shenvi

¹Department of Chemistry, The Scripps Research Institute , La Jolla, California 92037, United States.

Journal of the American Chemical Society

|November 15, 2014

Summary

Cobalt catalysts isomerize terminal alkenes and cyclize dienes. These catalysts also open strained rings, tolerating various functional groups like amines and epoxides.

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Area of Science:

Organometallic Chemistry
Catalysis
Organic Synthesis

Background:

Alkene isomerization is a fundamental transformation in organic chemistry.
Developing efficient and selective catalysts for alkene isomerization and related reactions is crucial.
Understanding catalyst behavior with diverse functional groups is key for practical applications.

Purpose of the Study:

To investigate the catalytic activity of Co(Sal(tBu,tBu))Cl with organosilanes for alkene isomerization.
To explore the scope of these catalysts in cycloisomerization of dienes and retrocycloisomerization of strained rings.
To assess the tolerance of the catalytic system towards various functional groups.

Main Methods:

Utilizing cobalt complexes, specifically Co(Sal(tBu,tBu))Cl, as catalysts.
Employing organosilanes as co-catalysts or activators.
Investigating reactions including terminal alkene isomerization, diene cycloisomerization, and strained ring opening.

Main Results:

Catalytic amounts of Co(Sal(tBu,tBu))Cl and organosilane irreversibly isomerize terminal alkenes by one position.
The catalytic system successfully effects cycloisomerization of dienes.
Retrocycloisomerization of strained rings was also achieved using the same catalysts.
The catalysts demonstrated tolerance towards strong Lewis bases (amines, imidazoles) and labile functionalities (epoxides).

Conclusions:

Co(Sal(tBu,tBu))Cl with organosilanes provides an effective catalytic system for alkene isomerization.
The catalyst system exhibits versatility, enabling diene cycloisomerization and strained ring opening.
The observed functional group tolerance expands the synthetic utility of this catalytic approach.