Alkanesulphonyl halides

Sulphenes, generated in situ from alkanesulphonyl halides and tertiary amines (equation 11), were the subject of much attention during the 1960s34, mainly concerning their addition to C=C bonds. Surprisingly, the addition of these ylids to carbonyl bonds... 

An example from another area of chemistry shows the versatility of the exchange method. Alkanesulphonyl halides react with deuteroalcohols to produce a deuterated sulphonate where only one deuterium [42] is replaced (never more than one). This... 

There are relatively few examples of the syntheses of aliphatic sultones by this mode of cydization. It relies on internal nucleophilic attack of oxygen at sulphonyl sulphur which has a good leaving group (e.g. a sulphonyl halide group). A recently reported case involves the cydization of co-hydroxy-1-alkanesulphonyl chlorides (equation 30)51. This method... 

Sulphonyl Halides and Sulphenes.—It is becoming clear that reactions of alkanesulphonyl chlorides in the presence of a tertiary amine are likely to give poor yields of simple sulphonation products, due to the formation of sulphenes (RCHaSOgCl RCH=SOa) and artefacts resulting from them. Electron-withdrawing groups in the substituent facilitate sulphene... 

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