A comparative study of the epoxidation of 2-substituted isoflavones by dimethyldioxirane, sodium hypochlorite, and alkaline hydrogen peroxide (Weitz-Scheffer reaction)

A. Lévai, T. Patonay, A. Szekely, E. B. Vass, W. Adam, J. Jekó́

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Abstract

The comparative epoxidation of 2-substituted isoflavones 9-16 has been conducted by the utilization of three different protocols, viz. epoxidation with isolated dimethyldioxirane (Method A), with sodium hypochlorite (Method B), and with alkaline hydrogen peroxide (Method C), to afford epoxides 17-24. Best results have been obtained with Method C (Weitz-Scheffer epoxidation). The structures of epoxides have been assigned on the basis of nmr spectral and mass spectral data.

Original languageEnglish
Pages (from-to)1065-1069
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume37
Issue number5
Publication statusPublished - 2000

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Sodium Hypochlorite
Isoflavones
Epoxidation
Hydrogen Peroxide
Epoxy Compounds
dimethyldioxirane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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T1 - A comparative study of the epoxidation of 2-substituted isoflavones by dimethyldioxirane, sodium hypochlorite, and alkaline hydrogen peroxide (Weitz-Scheffer reaction)

AU - Lévai, A.

AU - Patonay, T.

AU - Szekely, A.

AU - Vass, E. B.

AU - Adam, W.

AU - Jekó́, J.

PY - 2000

Y1 - 2000

N2 - The comparative epoxidation of 2-substituted isoflavones 9-16 has been conducted by the utilization of three different protocols, viz. epoxidation with isolated dimethyldioxirane (Method A), with sodium hypochlorite (Method B), and with alkaline hydrogen peroxide (Method C), to afford epoxides 17-24. Best results have been obtained with Method C (Weitz-Scheffer epoxidation). The structures of epoxides have been assigned on the basis of nmr spectral and mass spectral data.

AB - The comparative epoxidation of 2-substituted isoflavones 9-16 has been conducted by the utilization of three different protocols, viz. epoxidation with isolated dimethyldioxirane (Method A), with sodium hypochlorite (Method B), and with alkaline hydrogen peroxide (Method C), to afford epoxides 17-24. Best results have been obtained with Method C (Weitz-Scheffer epoxidation). The structures of epoxides have been assigned on the basis of nmr spectral and mass spectral data.

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