USE OF BETA-KETO SULFONES AS SYNTHETIC INTERMEDIATES

The β-keto sulfone 5 was found to be a more satisfactory intermediate than the corresponding β-keto sulfoxide 4 for the preparation of the tricyclic hydroxy ketone 1. Examination of several simpler β-keto sulfones 14, 16, and 18 indicated that the preparation and C-alkylation of these materials occur as readily as the reactions involving the corresponding β-keto sulfoxides. The β-keto sulfones are more stable to oxidation and reduction procedures than the β-keto sulfoxides. Although the β-keto sulfones can be reductively cleaved to form ketones in good yield, this cleavage process is more rapid with β-keto sulfoxides. © 1968, American Chemical Society. All rights reserved.