Reaction of alkyl halides with sulfites and sulfinic acids

Reaction of alkyl halides with sulfites and sulfinic acids 

Replacement of the halogen of alkyl halides by treatment with alkali sulfites was first used by Strecker340 in his preparation of aliphatic sulfonic acids  

Hemilian341 used ammonium sulfite on heating ethyl iodide (20 g) with a solution of crystalline ammonium sulfite (20 g) in water (40 ml) he obtained, after cooling, ammonium ethanesulfonate. To convert this into the barium salt he diluted it with water and heated it with lead oxide until evolution of ammonia ceased he filtered the mixture and removed the lead from the filtrate by hydrogen sulfide after renewed filtration he digested the filtrate with barium carbonate, filtered again, and evaporated that filtrate to dryness. 

Particularly good yields are obtained from n-alkyl halides, but only up to about 25% of the halide can be replaced from secondary carbon atoms, and tertiary halogen compounds give olefins. 

2-Ethanedisulfonic acid is obtained from ethylene dibromide and concentrated aqueous sodium sulfite solution,342 but using a deficiency of sulfite leads to sodium 2-bromoethanesulfonate.343 A general prescription for preparation of, co-alkanedisulfonates has been given by Stone.344 

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