ORGN 577 |
| Vinylketene iron(0) complexes react with a variety of alkyl, aryl, and functionalized chloroalkynes to form highly substituted chlorocatechols. Optimization of reaction conditions, regioselectivity, and product distribution will be discussed. Previous studies revealed that terminal aryl and alkylalkynes often failed to produce catechols, instead producing alkyne trimers and small amounts of insertion products, which failed to undergo reductive elimination. Chloroalkynes provide chlorocatechols with no trimer formation. Even the severely hindered 1-chloro-3,3-dimethylbutyne produces a single isomer in 38% yield with tricarbonyl(h4-2-ethoxy-3-phenylbuta-1,3-dienone)iron. Chloroethynylcyclopropane provided no rearrangement products and produced a mixture of cyclopropyl chlorocatechols. The scope and limitations of this methodology will be presented.
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Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster
Sci-Mix
Division of Organic Chemistry |
