Tetrahedron

Singlet oxygen and triazolinedione additions to α, β-unsaturated sulfoxides

T Akasaka, Y Misawa, M Goto, W Ando

Index: Akasaka, Takeshi; Misawa, Yoshihisa; Goto, Midori; Ando, Wataru Tetrahedron, 1989 , vol. 45, # 21 p. 6657 - 6666

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Citation Number: 34

Abstract

The reaction of singlet oxygen with 2-methyl-3-phenylsulfinyl-2-butene (1a) and E2- phenylsulfinyl-2-butene (1b) gives the corresponding allyl alcohols (2a and 2b) after reduction with dimethyl sulfide. α, β-Unsaturated sulfoxides with s-trans conformation failed to proceed the ene-type oxidation but afforded S-oxidation products. On the other hand, 4- methyl-1, 2, 4-triazoline-3, 5-dione (MeTAD) reacted with α, β-unsaturated sulfoxides (1a ...