Griesbaum coozonolysis

Griesbaum coozonolysis
Named after	Karl Griesbaum
Reaction type	Organic redox reaction
Identifiers
Organic Chemistry Portal	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][3][4][5]

Mechanism

The oxime first reacts with the ozone to form the corresponding carbonyl oxide, undergoes 1,3-dipolar cycloaddition with the carbonyl reactant to form the cyclic ozonide, as usual for the Criegee intermediate in the ozonolysis of alkenes.

If no carbonyl compound is used, the carbonyl oxide may dimerize and form 1,2,4,5-tetraoxanes.

References

Griesbaum, Karl; Övez, Bikem; Huh, Tae Sung; Dong, Yuxiang (1995). "Ozonolyses of O-methyloximes in the presence of acid derivatives: A new access to substituted ozonides". Liebigs Annalen. 1995 (8): 1571–1574. doi:10.1002/jlac.1995199508217.
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.
Griesbaum, Karl; Liu, Xuejun; Kassiaris, Athanassios; Scherer, Martin (1997). "Ozonolyses of O-Alkylated Ketoximes in the Presence of Carbonyl Groups: A Facile Access to Ozonides". Liebigs Annalen. 1997 (7): 1381–1390. doi:10.1002/jlac.199719970715.
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. PMID 15357611.
Chen, Jun; Gonciarz, Ryan L.; Renslo, Adam R. (2021). "Expanded scope of Griesbaum co-ozonolysis for the preparation of structurally diverse sensors of ferrous iron". RSC Advances. 11 (54): 34338–34342. Bibcode:2021RSCAd..1134338C. doi:10.1039/D1RA05932G. PMC 9042324. PMID 35497286.

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[1] Griesbaum, Karl; Övez, Bikem; Huh, Tae Sung; Dong, Yuxiang (1995). "Ozonolyses of O-methyloximes in the presence of acid derivatives: A new access to substituted ozonides". Liebigs Annalen. 1995 (8): 1571–1574. doi:10.1002/jlac.1995199508217.

[2] 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.

[3] Griesbaum, Karl; Liu, Xuejun; Kassiaris, Athanassios; Scherer, Martin (1997). "Ozonolyses of O-Alkylated Ketoximes in the Presence of Carbonyl Groups: A Facile Access to Ozonides". Liebigs Annalen. 1997 (7): 1381–1390. doi:10.1002/jlac.199719970715.

[4] 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. PMID 15357611.

[5] Chen, Jun; Gonciarz, Ryan L.; Renslo, Adam R. (2021). "Expanded scope of Griesbaum co-ozonolysis for the preparation of structurally diverse sensors of ferrous iron". RSC Advances. 11 (54): 34338–34342. Bibcode:2021RSCAd..1134338C. doi:10.1039/D1RA05932G. PMC 9042324. PMID 35497286.