Mechanistic Aspects and Profiles of the Double Elimination Reaction of β-Substituted Sulfones

Article abstract of DOI:10.1021/jo00370a016

The double elimination reaction of β-acetoxy or β-alkoxy sulfones was investigated in detail by employing some representative reactions.Successful isolation of reaction intermediates revealed the reaction path: the first step is elimination of the acetoxy group to afford a vinyl sulfone.The subsequent elimination of a phenylsulfonyl group from the vinyl sulfone gives acetylenes, while polyenes are formed in cases where isomerization of the vinyl sulfone to an allyl sulfone is possible prior to the second elimination.Besides these mechanistic considerations, general features are discussed in order to make clear the scope and limitations of this synthetically useful reaction.