Reactions of Unsaturated Sulphoxides and Selenoxides

Establishment of the absolute configuration of the sulphenate (23) that is formed from one enantiomer of a sulphoxide (24) gives a clear picture of the conformation of the reactant.  

The 5 n-elimination of sulphenic and selenenic acids from unsaturated sulphoxides and selenoxides introduces a further site of unsaturation, examples being the addition of allyl alcohols to allenic sulphoxides to give ff-(allyloxy)vinyl sulphoxides 

Masaki, K. Sakuma, and K. Kaji,7. Chem. Soc., Chem. Commun., 1980,434. 

Further Diels-Alder syntheses using yff-phenylsulphinyl-c ff-unsaturated carbonyl compounds (see Vol. 5, p. 39) have established these compounds as useful a -ethynylcarbonyl synthons, taking into account the scope for syn-elimination that is offered by the products. 

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