SINGLET OXYGEN AND TRIAZOLINEDIONE ADDITIONS TO α,β-UNSATURATED SULFOXIDES

Article abstract of DOI:10.1016/S0040-4020(01)89136-5

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.