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Volumn 60, Issue 5, 1995, Pages 1391-1407

Catalytic Epoxidation of Alkenes with Oxone

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EID: 0000225906     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00110a049     Document Type: Article
Times cited : (228)

References (104)
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  • 2
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    • Peroxomonosulfate, alternatively known as Caro's salt, caroate, or Oxone, is best represented by the formula 2KHS05 KHS04 K2S04 and is commercially available. The corresponding acid, Caro's acid, has been reported to detonate
    • Peroxomonosulfate, alternatively known as Caro's salt, caroate, or Oxone, is best represented by the formula 2KHS05 KHS04 K2S04 and is commercially available. The corresponding acid, Caro's acid, has been reported to detonate: Edwards, J. O. Chem. Eng. News 1955, 33, 3336.
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    • One of the elements of that design is an accurate knowledge of the preferred geometry of oxygen transfer in the transition state of dioxirane oxidations. We are currently investigating this issue independently (J. S. DePue, unpublished results). For a recent theoretical treatment of this problem see
    • One of the elements of that design is an accurate knowledge of the preferred geometry of oxygen transfer in the transition state of dioxirane oxidations. We are currently investigating this issue independently (J. S. DePue, unpublished results). For a recent theoretical treatment of this problem see: Bach, R. D.; Andrés, J. L.; Owensby, A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207.
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    • The epoxidation of alkenes with hydrogen peroxide can be catalyzed by ketones: hexafluoroacetone, (a)
    • The epoxidation of alkenes with hydrogen peroxide can be catalyzed by ketones: hexafluoroacetone, (a) Heggs, R. P.; Ganem, B. J.Am. Chem. Soc. 1979, 101, 2484;
    • (1979) J.Am. Chem. Soc. , vol.101 , pp. 2484
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    • hexachloroacetone, (b) U.S. Patent No. 4,247,948
    • hexachloroacetone, (b) Costerousse, G.; Teutsch, J. G. U.S. Patent No. 4,247,948; 1981.
    • (1981)
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    • The epoxidation of alkenes by Oxone in methanol without added ketones has been reported
    • The epoxidation of alkenes by Oxone in methanol without added ketones has been reported. Bloch, R.; Abecassis, J.; Hassan, D. J. Org. Chem. 1985, 50, 1544.
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    • An alternative procedure for formation of Af-alkyl, iV-methyl piperidinium salts was later developed which involved quaternization of commercially available Af-methyl-4-piperidinone with the appropriate rc-alkyl triflate. For the preparation of alkyl triflates see
    • An alternative procedure for formation of Af-alkyl, iV-methyl piperidinium salts was later developed which involved quaternization of commercially available Af-methyl-4-piperidinone with the appropriate rc-alkyl triflate. For the preparation of alkyl triflates see: Beard, C. D.; Baum, K. J. Org. Chem. 1974, 39, 3875.
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    • For a recent review of the Baeyer-Villiger oxidation see
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    • See for example Academic Press: New York
    • See for example Hanack, M. Conformation Theory, Academic Press: New York, 1965; pp 152-157.
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