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Using P.T.C.or cosolvents,both perfluoroalkyl iodides such as Cl(CF_2)_nI(n=2,4,6,1a-1c),H(CF_2)_8I(1d),CF_3(CF_2)_nI(n=3,5,7,1e-1g),and α,ω-perfluoroalkylene diiodides suchas(ICF_2CF_2)_2O(4a),I(CF_2)_nI(n=6,8,10,4b-4d)reacted smoothly with sodium dithionite in aqueoussolution under mild conditions to give the corresponding perfluoroalkanesulfinates Cl(CF_2)_nSO_2Na(n=2,4,6,2a-2c),H(CF_2)_8SO_2Na(2d),CF_3(CF_2)_nSO_2Na(n=3,5,7,2e-2g),α,ω-perfluoroalky-lenedisulfinates O(CF_2CF_2SO_2K)_2(5a),and KO_2S(CF_2))nSO_2K(n=6,8,10,6b-6d)in moderate tohigh yields.These sulfinates were converted to the corresponding sulfonyl chlorides by reacting withchlorine in the usual way.Thus the discovery of the new reagent renders sulfinatodeiodination apractical method for the synthesis of perfluorosulfinic and perfluorosulfonic acids and their derivativesfrom the corresponding perfluoroalkyl iodides.
Using PTCor cosolvents, both perfluoroalkyl iodides such as Cl (CF2) _nI (n = 2,4,6,1a-1c), H (CF_2) _8I (1d), CF_3 (CF_2) (A = 6,8,10,4b-4d), and α, ω-perfluoroalkylene diiodides suchas (ICF_2CF_2) _2O (4a), I (CF_2) _nI conditions to give the corresponding perfluoroalkanesulfinates Cl (CF_2) _nSO_2Na (n = 2,4,6,2a-2c), H (CF_2) _8SO_2Na (2d), CF_3 (CF_2) _nSO_2Na 2α, ω-perfluoroalky-lenedisulfinates O (CF_2CF_2SO_2K) _2 (5a), and KO_2S (CF_2)) nSO_2K (n = 6,8,10,6b-6d) in moderate to high yields.These sulfinates were converted to the corresponding sulfonyl chlorides by reacting with chlorine in the usual way. Thus the discovery of the new reagent renders sulfinatodeiodination apractical method for the synthesis of perfluorosulfinic and perfluorosulfonic acids and their derivatives from the corresponding perfluoroalkyl iodides.