Facile One Pot Thermal Dehydration and Dethioacetalization of β-Hydroxydithioacetals with Dimethyl sulphoxide: Synthesis of α,β-Unsaturated Aldehydes

Article abstract of DOI:10.1016/S0040-4020(01)85646-5

The acyclic and cyclic β-hydroxydithioacetals 3a-m and 4a-b obtained by sodium borohydride reduction (or Grignard addition) of the corresponding β-oxodithioacetals 2a-m are shown to undergo facile one pot thermal dehydration and dethioacetalization in the presence of dimethyl sulphoxide to afford the corresponding ene- and polyene aldehydes 5a-m and 6a-b in good yields.The probable mechanism of dethioacetalization with dimethyl sulphoxide has also been discussed.