Reactions of Acrolein and Related Compounds. VIII. Preparation of Sultones

The Chemistry of Sultones and Sultams.

“…The general method for the preparation of sultones consists in the elimination of the elements of water from the corresponding hydroxysulfonic acid, either by the action of heat (1,32,33,65) or of a mixture of concentrated sulfuric acid and acetic anhydride (46,47) or by boiling the diazotized solution of an oor periaminoarylsulfonic acid (18, 45).…”

“…OqHsOSOa then H20 and BaCO, (R'CH=CRCH2S03)2Ba The treatment of ,ß-unsaturated aldehydes with sodium bisulfite, followed by reduction with Raney nickel, hydrolysis of the sodium salt, and heating, gives the corresponding sultone (65). Only two sultones-namely, -propanesultone (XIHa: R = R' = X = H) and d-methyl-y-propanesultone (XIHa: R = CHS, R' = X = H)-have been prepared by this method.…”

Propanesultone

“…The water formed may be removed by distillation (simple or azeotropic, with xylene) (33). The required y-hydroxypropanesulfonic acid is prepared from the sodium salt, in turn available from addition of sodium bisulfite to acrolein, followed by reduction (3,30) or by air-catalyzed addition of bisulfite to allyl alcohol (19). For the reduction reaction, over-all yield is 79%; for the addition reaction, 85%.…”

Progress in the synthesis of δ-sultones

“…In contrast to the syntheses of lactones from the corresponding hydroxycarboxylic acids by classical esterification methods, sultones can in general not be accessed by such strategies [ 2 , 14 – 19 ]. The early synthesis approaches mainly relied on the direct distillation of halo- or hydroxysulfonic acids under vacuum [ 14 – 17 ] to give 5–7 membered-ring sultones or on sulfonation reactions of alkenes with SO 3 (for pioneering reports by Bordwell et al, see [ 18 , 19 ]) (Scheme 1 ). The later method even allows for the synthesis of highly reactive β-sultones, and over the years, these methods have been significantly developed further [ 2 – 6 ].…”