1-(Phenylthio)- and 1-(phenylsulfoxide)-4-alkoxy-butadienes, a new class of chiral dienes

Article abstract of DOI:10.1016/S0040-4039(00)92218-4

Trans-acetalization of the methyl acetal of 3-methyl-4-(phenylthio)-but-2-enal 2a in acidic medium leads to the expected trans-acetals 2b-f or their γ-elimination products (i.e. 4-alkoxy-2-methyl-1-(phenylthio)buta-1,3-dienes 4), depending on the nature of the selected alcohol. Both types of compounds may be easily oxidized into the expected sulfoxides 6. The menthyloxy and phenyl-8-menthyloxy sulfides 4b,c and sulfoxides 6b,c have been prepared.