Alkylation and acylation of 5-phenylsulphonyl- and 5-cyanobutyrolactones

Conditions are reported for the alkylation and acylation alpha to the sulphonate of a butyrolactone carrying a 5-phenylsulphonyl group. Yields are good if the alkyl or acyl halide is sufficiently reactive. The phenylsulphonyl group is initially retained and studies of its elimination are described. The corresponding system with nitrile in place of phenylsulphonyl appears to be a less satisfactory synthon for the desired chemistry.