Synthesis of tetrasubstituted ozonides by the Griesbaum coozonolysis reaction: Diastereoselectivity and functional group transformations by post-ozonolysis reactions

Yuanqing Tang, Yuxiang Dong, Jean M. Karle, Charles A. DiTusa, Jonathan L. Vennerstrom

Research output: Contribution to journalArticle

65 Citations (Scopus)

Abstract

The diastereoselectivity of the Griesbaum coozonolysis reaction with O-methyl 2-adamantanone oxime and 4-substituted cyclohexanones reveals that the major tetrasubstituted ozonide isomers possess cis configurations, suggesting a preferred axial attack of the carbonyl oxide on the cyclohexanone dipolarophiles. It is evident that these tetrasubstituted ozonides are quite stable to triphenylphosphine, borohydrides, hydrazine, alkyllithiums, Grignard reagents, mercaptides, and aqueous KOH as illustrated by the synthesis of amine, alcohol, acid, ester, ether, sulfide, sulfone, and heterocycle-functionalized ozonides by a wide range of post-ozonolysis transformations.

Original languageEnglish (US)
Pages (from-to)6470-6473
Number of pages4
JournalJournal of Organic Chemistry
Volume69
Issue number19
DOIs
StatePublished - Sep 17 2004

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Functional groups
hydrazine
Cyclohexanones
Borohydrides
Sulfones
Oximes
Sulfides
Isomers
Ether
Oxides
Amines
Esters
Alcohols
Acids
1,2,4-trioxane
cyclohexanone
triphenylphosphine
adamantanone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Synthesis of tetrasubstituted ozonides by the Griesbaum coozonolysis reaction: Diastereoselectivity and functional group transformations by post-ozonolysis reactions",
abstract = "The diastereoselectivity of the Griesbaum coozonolysis reaction with O-methyl 2-adamantanone oxime and 4-substituted cyclohexanones reveals that the major tetrasubstituted ozonide isomers possess cis configurations, suggesting a preferred axial attack of the carbonyl oxide on the cyclohexanone dipolarophiles. It is evident that these tetrasubstituted ozonides are quite stable to triphenylphosphine, borohydrides, hydrazine, alkyllithiums, Grignard reagents, mercaptides, and aqueous KOH as illustrated by the synthesis of amine, alcohol, acid, ester, ether, sulfide, sulfone, and heterocycle-functionalized ozonides by a wide range of post-ozonolysis transformations.",
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T1 - Synthesis of tetrasubstituted ozonides by the Griesbaum coozonolysis reaction

T2 - Diastereoselectivity and functional group transformations by post-ozonolysis reactions

AU - Tang, Yuanqing

AU - Dong, Yuxiang

AU - Karle, Jean M.

AU - DiTusa, Charles A.

AU - Vennerstrom, Jonathan L.

PY - 2004/9/17

Y1 - 2004/9/17

N2 - The diastereoselectivity of the Griesbaum coozonolysis reaction with O-methyl 2-adamantanone oxime and 4-substituted cyclohexanones reveals that the major tetrasubstituted ozonide isomers possess cis configurations, suggesting a preferred axial attack of the carbonyl oxide on the cyclohexanone dipolarophiles. It is evident that these tetrasubstituted ozonides are quite stable to triphenylphosphine, borohydrides, hydrazine, alkyllithiums, Grignard reagents, mercaptides, and aqueous KOH as illustrated by the synthesis of amine, alcohol, acid, ester, ether, sulfide, sulfone, and heterocycle-functionalized ozonides by a wide range of post-ozonolysis transformations.

AB - The diastereoselectivity of the Griesbaum coozonolysis reaction with O-methyl 2-adamantanone oxime and 4-substituted cyclohexanones reveals that the major tetrasubstituted ozonide isomers possess cis configurations, suggesting a preferred axial attack of the carbonyl oxide on the cyclohexanone dipolarophiles. It is evident that these tetrasubstituted ozonides are quite stable to triphenylphosphine, borohydrides, hydrazine, alkyllithiums, Grignard reagents, mercaptides, and aqueous KOH as illustrated by the synthesis of amine, alcohol, acid, ester, ether, sulfide, sulfone, and heterocycle-functionalized ozonides by a wide range of post-ozonolysis transformations.

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