Tetrahedron p. 6657 - 6666 (1989)
Update date:2022-08-05
Topics:
Akasaka, Takeshi
Misawa, Yoshihisa
Goto, Midori
Ando, Wataru
The reaction of singlet oxygen with 2-methyl-3-phenylsulfinyl-2-butene (1a) and E-2-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-triazole-3,5-dione (MeTAD) reacted with α,β-unsaturated sulfoxides (1a and 1b) and E-2-ethylidenethiolan-1-oxide (1g) to give the corresponding allyl triazolidines as ene-type products.
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