Thiophilic addition of organolithiums to aliphatic sulfines

Article abstract of DOI:10.1016/0040-4039(96)00869-6

Enethiolizable sulfines, freshly generated by oxidation of dithioesters, have been reacted with organolithiums. The reaction follows a selective thiophilic course leading to stabilised dithioacetal oxide carbanions, which have been subsequently treated with electrophiles. The resulting dithioacetal oxides are readily transformed into aldehydes or spontaneously to ketones. The specificity of this 'Umpolung' related chemistry is that it involves an addition reaction and not a deprotonation. Carbophilic addition has not been evidenced and enethiolization appears very limited.