ORGN 645 |
Study of an uncommon radical fragmentation to form acyl radicals
| Tiffany R. Turner and Dennis Curran. Department of Chemistry, University of Pittsburgh, Chevron Science Center, 219 Parkman Ave., Pittsburgh, PA 15260 |
| Recently, Uta Wille and coworkers proposed a novel non-chain, self-terminating, oxidative radical cyclization that ends with the uncommon homolytic cleavage of an acyl-oxygen bond to give a ketone and an acyl radical. We present the results of our study into this type of unusual radical fragmentation. Our focus was on initiating radical intermediates 1 through thermal means using Bu3SnH to produce ketone 2 as opposed to photo-induced methods used by Wille. In our work, we were unable to produce 2 in sufficient yields, but we were able to isolate carbonyl compounds 3. Based on these results, we cannot rule out an alternative polar fragmentation. 
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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