Griesbaum coozonolysis
The Griesbaum coozonolysis is a name reaction in organic chemistry that allows for the preparation of tetrasubstituted ozonides (1,2,4-trioxolanes) by the reaction of O-methyl oximes with a carbonyl compound in the presence of ozone. Contrary to their usual roles as intermediates in ozonolysis and other oxidative alkene cleavage reactions, 1,2,4-trioxolanes are relatively stable compounds and are isolable.[1][2]
Griesbaum coozonolysis
| Griesbaum coozonolysis | |
|---|---|
| Named after | Karl Griesbaum |
| Reaction type | Organic redox reaction |
| Identifiers | |
| Organic Chemistry Portal | griesbaum-coozonolysis |
Mechanism
The oxime first reacts with the ozone to form the corresponding carbonyl oxide, which undergoes 1,3-dipolar cycloaddition with the carbonyl molecule to form the tetrasubstituted ozonide.
If no carbonyl compound is used, the carbonyl oxide may dimerize and form 1,2,4,5-tetraoxanes.
References
- Griesbaum, Karl; Liu, Xuejun; Dong, Yuxiang (14 April 1997). "Diozonides from coozonolyses of suitable O-methyl oximes and ketones". Tetrahedron. 53 (15): 5463–5470. doi:10.1016/S0040-4020(97)00260-3.
- Tang, Yuanqing; Dong, Yuxiang; Karle, Jean M.; DiTusa, Charles A.; Vennerstrom, Jonathan L. (19 August 2004). "Synthesis of Tetrasubstituted Ozonides by the Griesbaum Coozonolysis Reaction: Diastereoselectivity and Functional Group Transformations by Post-Ozonolysis Reactions". The Journal of Organic Chemistry. 69 (19): 6470–6473. doi:10.1021/jo040171c.
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