ORGN 19 |
| Martin G. Kociolek, Kyle P. Kalbarczyk, Nicholas G. Straub, Jolene V. Schuster, and Elizabeth J. Marton. Science, Penn State Erie, The Behrend College, 31 Hammermill Building, 5091 Station Road, Erie, PA 16563-0107 |
| Isoxazolines and isoxazoles have long been recognized as versatile synthetic intermediates for the construction of a variety of 1,3-difunctionalized compounds. Our ongoing investigations into novel ring-opening reactions of these heterocycles will be presented. We have shown that a variety of substituted 3-bromo-2-isoxazolines can be opened with sodium iodide and either chlorotrimethylsilane or para-toluenesulfonic acid, to give 3-hydroxynitriles in 68-90% yields. We have also demonstrated that substituted 3-bromo-2-isoxazoles can be cleaved with molybdenum hexacarbonyl to give 2-cyanoketones in 58-75% yields. In addition, the preliminary results of our investigations into the tandem ring-opening/aldol condensation of 3-bromo-2-isoxazoles, as well as the ring opening of 3-alkoxy and 3-amino-2-isoxazoles, will be discussed.
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New Reactions and Methodology
8:00 AM-12:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- 303A, Oral
Division of Organic Chemistry |