Abstract
The 2,3-sigmatropic rearrangements are involved in the preparation of allenyl sulphoxides. The method consists of reaction of a propargylic alcohol with a sulphenyl chloride in the presence of triethylamine. The initially formed product undergoes a 2,3-sigmatropic rearrangement at low temperatures to afford the allenic sulphoxide. The formation of the strong S–O bond is the driving force and yields are generally high. This chapter presents the schemes showing reactions between propargylic alcohols and sulphinyl chlorides or trivalent phosphorus chlorides. The 3,3-sigmatropic rearrangements are also involved in affording an allenic system. Such an allenic system can be isolated as a relatively stable compound, however in many cases one is concerned with a short-living molecule, which polymerizes or cyclizes, unless it is trapped with a reactive reagent. The chapter presents the mechanism involved in 3,3-sigmatropic rearrangements. It also discusses the synthesis of a number of compounds based on these two rearrangements, some of these are methyl 1,2-propadienyl sulphoxide from propargyl alcohol and methanesulphenyl chloride, phenyl 1,2-propadienyl sulphoxide from benzenesulphenyl chloride and propargyl alcohol, and methyl 3-methyl-1,2-butadienyl sulphone from 2-methyl-3-butyn-2-ol and methanesulphinyl chloride.
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