Epoxidation of flavones by dimethyldioxirane

Waldemar Adam, Dieter Golsch, Lazaros Hadjiarapoglou, T. Patonay

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported. These labile epoxides were isolated and completely characterized by UV, IR, 1H and 13C NMR, MS, and C, H analyses. Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n. Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f as a mixture of cis and trans isomers.

Original languageEnglish
Pages (from-to)7292-7297
Number of pages6
JournalJournal of Organic Chemistry
Volume56
Issue number26
Publication statusPublished - 1991

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Flavones
Epoxidation
Epoxy Compounds
Acetone
Isomers
Methanol
Nuclear magnetic resonance
Temperature
dimethyldioxirane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Adam, W., Golsch, D., Hadjiarapoglou, L., & Patonay, T. (1991). Epoxidation of flavones by dimethyldioxirane. Journal of Organic Chemistry, 56(26), 7292-7297.

Epoxidation of flavones by dimethyldioxirane. / Adam, Waldemar; Golsch, Dieter; Hadjiarapoglou, Lazaros; Patonay, T.

In: Journal of Organic Chemistry, Vol. 56, No. 26, 1991, p. 7292-7297.

Research output: Contribution to journalArticle

Adam, W, Golsch, D, Hadjiarapoglou, L & Patonay, T 1991, 'Epoxidation of flavones by dimethyldioxirane', Journal of Organic Chemistry, vol. 56, no. 26, pp. 7292-7297.
Adam W, Golsch D, Hadjiarapoglou L, Patonay T. Epoxidation of flavones by dimethyldioxirane. Journal of Organic Chemistry. 1991;56(26):7292-7297.
Adam, Waldemar ; Golsch, Dieter ; Hadjiarapoglou, Lazaros ; Patonay, T. / Epoxidation of flavones by dimethyldioxirane. In: Journal of Organic Chemistry. 1991 ; Vol. 56, No. 26. pp. 7292-7297.
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