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

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: http://en.wikipedia.org/wiki/Olefin_metathesis Other References: "BIg Deal Reaction (ACS)”, Mechanism and More

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, 10978. Ring Opening Metathesis Truett, et al. JACS, 1960, 19, 2337. Cross Metathesis Zhang et al. JACS, 1993, 115, 10998. Wiki Page: http://en.wikipedia.org/wiki/Olefin_metathesis Other References: "BIg Deal Reaction (ACS)”, Mechanism and More

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

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”

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

Solutions 1- 2- 3-

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