CHED 1216 |
The chemistry of donor-functionalized cyclopentadienyl metal carbonyl anions is a research focus of the Fischer group. Novel intramolecular hydrogen bonds involving group VI metal acceptors in zwitterionic (2-(dimethylammonium)ethyl)cyclopentadienyltricarbonylmetalates, M(CO)3(CpNH) (M = Cr, Mo, W) prompted us to explore methylation of (2-(dimethylamino)ethyl)cyclopentadienyl group VI metal carbonyl anions in the hopes of selective attack at the amine resulting in zwitterionic (2-(trimethylammonium)ethyl)cyclopentadienyltricarbonylmetalates, M(CO)3(CpNMe). Reactions of CH3I and these anions resulted in metal alkyls; addition of excess CH3I led to doubly methylated salts [M'CH3(CO)3(CpNMe)]I (M' = Mo, W). These results suggested that a protecting group was necessary for the metal to permit selective methylation of the amine, and the pursuit of this hypothesis was our objective in summer 2006. Oxidation of Na[M(CO)3(CpN)] with iodine provides MI(CO)3(CpN); subsequent methylation affords structurally characterized [MI(CO)3(CpNMe)]I. Reduction of these salts provides structurally characterized (2-(trimethylammonium)ethyl)cyclopentadienyltricarbonylmetalates. The spectroscopic and structural properties of these zwitterions, and their nucleophilicity, will be discussed.
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Undergraduate Research Poster Session: Inorganic Chemistry
2:00 PM-4:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Chemical Education |