Electrophilic metallocenium ion-pairs catalyzed selective arene alkylation of alpha-chloronorbornene

ORGN 367

Aswini K. Dash, aswini@chem.northwestern.edu and Tobin J. Marks. Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-3113
Single-site catalysts for the coordinative/insertive polymerization of non-polar olefins have been extensively studied, however, very little is known for the corresponding polymerization of polar monomers. Development of catalysts for the insertive polymerization/co-polymerization of polar monomers (e.g., vinyl chloride) is of great interest because of the possibility that the polymer composition, microstructure, and molecular weight can be controlled by manipulation of catalyst and co-catalyst structure. The unsuccessful attempts to polymerize vinyl chloride using single-site catalysts is due to beta-Cl elimination after the first insertion of the monomer. We anticipated that the insertion of alpha-chloronorbornene into metal-alkyl ion-pairs should disfavor the syn-periplanar metal-chlorine configuration necessary for beta-Cl elimination. This poster will describe the results from the reaction of different metallocene ion-pairs with norbornene chloride, that leads to the formation of Friedel-Craft alkylation products with aromatic reagents. The process is catalytic with high turn-over frequencies.

Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster

8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005