ORGN 603 |
1,2,4-Trioxepanes as redox sensitive protecting groups for carbonyls
| Aqeel Ahmed and Patrick H. Dussault. Department of Chemistry, University of Nebraska-Lincoln, 643 Hamilton Hall, Lincoln, NE 68588-0304 |
| 1,2,4-Trioxepanes, available in high yield through reaction of aldehydes or ketones with 3-triethylsilyldioxy-3-methyl butanol or the corresponding triethylsilyl ether, are stable to a variety of synthetic conditions (acid, mild base, heat, many nucleophiles) but are easily cleaved upon treatment with Mg/MeOH or Zn/AcOH. The reactivity profile of the trioxepanes suggests they may complement the use of 1,3-dithianes for carbonyl protection. 
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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
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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