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The reaction of perfluoroalkanesulfinates: IV. Perfluoroalkyl radical addition to olefins initiated by single electron oxidation of perfluoroalkanesulfinate
Author(s) -
WeiYuan Huang,
Yuan Xie
Publication year - 1990
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19900080414
Subject(s) - chemistry , oxidizing agent , adduct , radical , medicinal chemistry , solvent , redox , organic chemistry
Sodium perfluoroalkanesulfinates [Cl (CF 2 ) n SO 2 Na (1), a , n = 4; b , n = 6; c , n = 8] with the reduction potentials about 0.95—1.00V could be oxidized readily with various oxidizing agents such as Mn (OAc) 3 2H 2 O, Ce (SO 4 ) 2 , HgSO 4 and Co 2 O 3 to generate perfluoroalkyl radicals which added to the olefins RCH CHR' to give two kinds of adducts, namely RCH (R f ) CHXR' (3, X H; 4, X OAc), with good yields depending upon the solvent system used. Different oxidizing agents showed slight variation on the yields of the adducts. The reaction time could be greatly shortened at higher temperature. Thus, this reaction provides a new way for introducing a perfluoroalkyl group into olefinic compounds.