Amides from sulphonyl halides

Amides are the least reactive of the carboxylic acid derivatives, and undergo acid or base hydrolysis to produce the parent carboxylic acids, and reduction to appropriate amines (see Section 4.3.10). They can also be dehydrated to nitriles, most commonly with boiling acetic anhydride, (AcO)20, sulphonyl chloride (SOCI2) or phosphoms oxychloride (POCI3) (see Section 4.3.18). Amines (with one less carbon) are prepared from amides by the treatment of halides (Br2 or CI2) in aqueous NaOH or KOH. This reaction is known as Hofmann rearrangement (see Section 4.3.10). 

The reactions of sulphimides studied recently concern the kinetics of the reaction between PhSH and JV-toluene-p-sulphonyl-sulphimides - to give PhSSPh, or RSPh (other differences exist between the results from these two studies) the formation of vinyl sulphides by treatment of JV-toluene-p-sulphonyl aryl ethyl sulphimides with Bu OK [TsN=S(Et)Ar -> CHg= CHSAr] the halide-ion-induced Stevens-type rearrangement to the sulphen-amide [TsN=SRAr -> RN(Ts)SAr] and the S-substitution or Pummerer rearrangement products from iV-toluene-/j-sulphonyl-sulphimides by cleavage with NaOH or NaOMe in MeOH. °... 

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