ORGN 399 |
Synthesis of functionalized ozonides by post-ozonolysis reactions
| Yuanqing Tang, Yuxiang Dong, and Jonathan L. Vennerstrom. Department of Pharmaceutical Sciences, University of Nebraska Medical Center, Omaha, NE 68198-6025 |
| Tetrasubstituted ozonides are in general difficult to obtain via the traditional approach, that is, ozonolysis of an alkene in an aprotic solvent. The prediction that di- and tri-substituted ozonides, readily available from the olefinic route, are significantly less stable than tetrasubstituted ozonides wasn't fully substantiated until new avenues to these ozonides were recently developed by Griesbaum. However, the challenge for the synthesis of functionalized tetrasubstituted ozonides remains, since the scope of ozonide compatible synthetic transformations has not been thoroughly investigated. We found that in contrast to other peroxides, including simple ozonides that are easily cleaved by reducing agents or by reactive organometallics, tetrasubstituted ozonides are relatively robust, allowing for a range of chemical transformations such as reductions, Mitsunobu reactions, and nucleophilic substitutions. The intermediate ozonide (1) was prepared via Griesbaum coozonolysis by treating O-methyl 2-adamantanone oxime with ozone in the presence of ethyl 4-cyclohexanonecarboxylate. Transformations of the ester group provided ozonide derivatives (2) containing hydroxy, amine, ether, and thioether functional groups.  |
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Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, September 8, 2003 Javits Convention Center -- North Pavillion, Sci-Mix
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
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