Dioxirane oxidation of (Z)-1-thioaurones, (E)-3-arylidene-1-thiochroman-4-ones and (E)-3-arylidene-1-thioflavan-4-ones

Waldemar Adam, Dieter Golsch, Lazaros Hadjiarapoglou, A. Lévai, Csaba Nemes, T. Patonay

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The oxidation of the title compounds 1, 4 and 7 with dimethyldioxirane (DMD) afforded the corresponding sulfoxides 2, 5 and 8 and/or sulfones 3, 6 and 9 in good yields (Scheme 1 and 2). Excess dimethyldioxirane gave the sulfones chemoselectively without formation of the epoxides. The epoxidation of the sulfones 6a,b,d to the respective spiroepoxides 10a,b,d required the more reactive methyl(trifluoromethyl)dioxirane (TFD) as oxidant.

Original languageEnglish
Pages (from-to)13113-13120
Number of pages8
JournalTetrahedron
Volume50
Issue number46
DOIs
Publication statusPublished - 1994

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Sulfones
Oxidation
Sulfoxides
Epoxidation
Epoxy Compounds
Oxidants
dioxirane
dimethyldioxirane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Dioxirane oxidation of (Z)-1-thioaurones, (E)-3-arylidene-1-thiochroman-4-ones and (E)-3-arylidene-1-thioflavan-4-ones. / Adam, Waldemar; Golsch, Dieter; Hadjiarapoglou, Lazaros; Lévai, A.; Nemes, Csaba; Patonay, T.

In: Tetrahedron, Vol. 50, No. 46, 1994, p. 13113-13120.

Research output: Contribution to journalArticle

Adam, Waldemar ; Golsch, Dieter ; Hadjiarapoglou, Lazaros ; Lévai, A. ; Nemes, Csaba ; Patonay, T. / Dioxirane oxidation of (Z)-1-thioaurones, (E)-3-arylidene-1-thiochroman-4-ones and (E)-3-arylidene-1-thioflavan-4-ones. In: Tetrahedron. 1994 ; Vol. 50, No. 46. pp. 13113-13120.
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