Regio- and Stereoselective Synthesis of Substituted 2-(Phenylthio)-1,3-butadienes

Article abstract of DOI:10.1021/jo00229a008

Sulfur-substituted 1,3-butadienes are useful reagents in organic synthesis.We now report two general methods for the regio- and stereoselective synthesis of substituted 2-(phenylthio)-1,3-butadienes 4 and 5. 3-(Phenythio)-3-sulfolenes 2 can be specifically alkylated at C5 under basic conditions.Extrusion of sulfur dioxide by lithium aluminum hydride then gives the dienes 4.On the other hand 2-substituted 3-sulfolenes 11 can be converted to the 3-phenylthio derivatives 9, which upon heating give the dienes 5.