Tetrahedron

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

…, L Hadjiarapoglou, A Lévai, C Nemes, T Patonay

Index: Adam, Waldemar; Golsch, Dieter; Hadjiarapoglou, Lazaros; Levai, Albert; Nemes, Csaba; Patonay, Tamas Tetrahedron, 1994 , vol. 50, # 46 p. 13113 - 13120

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Citation Number: 35

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.