Sulphones in Synthesis

Thermal pericyclic rearrangement of an aryl allyl sulphone ArSOzCR R -CR =CR R at ca. 290 C places the aryl substituent at the y-position of the allylic system, SO2 being eliminated to give ArCR R CR =CR R. Isomerization to the vinyl sulphone can occur with t-butyl allyl sulphones on treatment with K2CO3 in acetone. 

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Reactions of Saturated Sulphones.—Applications of sulphones in synthesis are discussed in a later section, and sulphonyl-stabilized carbanions are dealt with elsewhere in this Volume. This section is therefore concerned with reactions of saturated alkyl and aryl sulphones, particularly C—S bond cleavage reactions, on which many applications of sulphones in synthesis depend. 

Uses of Sulphones in Synthesis.—In acid-promoted ring-opening reactions of a-hydroxyalkylcyclopropanes (68), the concentrated bulk of the PhS02 group... 

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