ORGN 1 |
| Keith A. Woerpel, Stacie A. Calad, Jelena Cirakovic, T. B. Clark, Tom G. Driver, and Sarah G. Ludlum. Department of Chemistry, University of California, Irvine, Irvine, CA 92697-2025 |
| A silver-catalyzed synthesis of silacyclopropanes has been developed that involves silylene transfer from a highly reactive silacyclopropane to another alkene. These reactions proceeded rapidly at –27 °C with mono- and disubstituted alkenes, and the reactions occurred stereospecifically and diastereoselectively. Silver catalysts can transfer dialkylsilylene units to other organic functional groups, leading to other silicon-containing products with high selectivity. Mechanistic information implicates metal silylenoid intermediates. For all of the products formed by silylene transfer, in situ functionalization provides access to polyoxygenated organic structures after oxidation of the carbon-silicon bond. |
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James Flack Norris Award in Physical Organic Chemistry
8:35 AM-12:00 PM, Sunday, March 23, 2003 Convention Center -- La Nouvelle Ballroom A/B, Oral
Division of Organic Chemistry |