1. Olefin Metathesis Created by Elizabeth Billings
Edited by Margaret Hilton
Honors Organic Chemistry
Chem 2321 (Sigman), 2013

2. Olefin Metathesis Mechanism
Overview: Olefin metathesis is a powerful reaction catalyzed by transition metals, in which two olefins can form a ring or rearrange their connectivity, or a double bond in a ring can be opened. These types of metathesis are called ring closing metathesis, cross metathesis or ring opening polymerization, respectively.
Mechanism
Wiki Page:
Other References: "BIg Deal Reaction (ACS)”, Mechanism and More

3. Olefin Metathesis Types of Metathesis
Overview: Olefin metathesis is a powerful reaction catalyzed by transition metals, in which two olefins can form a ring or rearrange their connectivity, or a double bond in a ring can be opened. These types of metathesis are called ring closing metathesis, cross metathesis or ring opening polymerization, respectively.
Types of Metathesis
Ring Closing Metathesis
Forbes et al. JACS, 1992, 114,
Ring Opening Metathesis
Truett, et al. JACS, 1960, 19, 2337.
Cross Metathesis
Zhang et al. JACS, 1993, 115,
Wiki Page:
Other References: "BIg Deal Reaction (ACS)”, Mechanism and More

4. Catalysts Titanium Tungsten Molybdenum Ruthenium Aldehydes Olefins
Ketones
Esters, Amides
References: 2005 Nobel Prize Lecture and Slides

5. Ring Opening Polymerization: Ballistic Protection
DCPD, when imbedded with a chemical catalyst, is considered a “self-healing polymer.” When it is hit, the catalytic trigger is activated and the resulting cracks are filled in with newly formed polymer via ring-opening metathesis. This makes it incredibly strong, as well as potentially useful in combat situations.
9 mm bullets stopped by DCPD
References: ”Self-Healing Composite Armor”, ”New Developments in Olefin Metathesis Technology”

6. Problems
References: 1- Fürstner, Alois et al. CEJ, 2013, 2- Grubbs, et al. Tetrahedron, 2004, 60, 7117,
3- Grubbs, et al. JACS, 1993, 115, 9856

7. Solutions 1- 2- 3-

8. Contributed by: Created by Elizabeth Billings
Edited by Margaret Hilton
Honors Organic Chemistry
Chem 2321 (Sigman), 2013
University of Utah