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, 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; 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.
^ 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. doi:10.1039/D1RA05932G.

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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.

[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. doi:10.1039/D1RA05932G.

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