Abstract
Sulfonyldiazomethanes (1), as stable and safe substitutes for hazardous diazomethane, have been conveniently acylated with acyl chlorides in the presence of triethylamine in acetonitrile to give α-acylsulfonyldiazomethanes (α-diazo-β-ketosulfones, 3) in good yields. Investigation of their thermal behavior in the presence of benzyl alcohol has revealed that Wolff rearrangement occurs to give α-sulfonylacetates (4). The overall process may provide a new, safe method for the Arndt-Eistert synthesis of α-sulfonylacetates (4) from carboxylic acid chlorides.
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