ORGN 486 |
| Ozonolysis is a powerful methodology for oxidative cleavage of alkenes. However, alkene ozonolysis typically generates ozonides or related peroxides which, while frequently isolable, are prone to spontaneous and dangerously exothermic decomposition reactions. Consequently, most ozonolysis reactions must be followed by a separate reduction or fragmentation. As part of efforts to expand the synthetic applications of alkene ozonolysis, we have become interested in reagents capable of capturing and decomposing the transient carbonyl oxide reaction intermediates, avoiding generation or accumulation of ozonides or other peroxide intermediates. Our research has discovered that capture of carbonyl oxides by amine-N-oxides directly generates aldehydes, providing an efficient one-pot "reductive" ozonolysis of alkenes.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
