ORGN 130 |
| Kelsie J Betsch, Chemistry, Augustana College, Sioux Falls, SD, 2001 S. Summit Ave, Sioux Falls, SD 57197 and Jetty Duffy-Matzner, Augustana College. |
| Numerous macrocyclic compounds are biologically active in the selective trapping and transport of sodium or potassium ions. We are interested in the synthesis of possible monomers to be used in the production of novel tetraester macrocyclic compounds. A generic monomer could consist of a 3,4-derivatized tetrahydrofuran, and it has been discovered that 2H,5H-dihydrofuran-3-yl ketones would make probable precursors to these monomers. A large emphasis has been placed on varying the substituents in the 2 and 5 positions of the tetrahydrofuran ring and studying the effects on the diastereotopic selectivity of the intramolecular silyl olefin cycloaddition (ISOC), and long-range proton coupling of the ensuing 2H,5H-dihydrofuran-3-yl ketones. We explored several different substituents to see the electronic and steric effects of said substituents upon the 4J and 5J bond coupling. The necessary propargylic alcohols have been prepared via Grignard reactions, and then undergone Michael additions with various nitro compounds to form nitroethers. These nitroethers were then cyclized via ISOC to form the dihydrofuroketones. Specifically, 2-methylhex-4-yn-3-ol, 1-phenyl-2-butyn-1-ol, and 3-pentyn-2-ol have been added to â-nitrostyrene, nitroethylene, and 3,3-dimethyl-1-nitrobutene, respectively, to create 2-[1-[1-methylethyl]-2-butynoxy]-2-phenyl-1-nitroethane, 2-[1-phenyl-2-butynoxy]-1-nitro-ethane, and 2-[1-methyl-2-butynoxy]-3,3-dimethyl-1-nitrobutane. From these nitroethers via ISOC, 1-[2-[1-methylethyl]-5-phenyl-2H,5H-dihydrofuran-3-yl]-ethanone, 1-[2-phenyl-2H,5H-dihydrofuran-3-yl]-ethanone, and 1-[2-methyl-5-[1,1-dimethylethyl]-2H,5H-dihydrofuran-3-yl]-ethanone have been synthesized. All compounds have been fully characterized by FTIR, GCMS, 1H NMR, and 13C NMR. |
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New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Sci-Mix
Division of Organic Chemistry |