Premium
The syntheses of fluorinated alkanesulfonamides and poly‐(fluorinated alkanesulfonamides)
Author(s) -
WeiYuan Huang,
ChangMing Hu,
HengYao Lu
Publication year - 1983
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19830010110
Subject(s) - chemistry , condensation polymer , monomer , iodide , chloride , polymer chemistry , polymer , sulfonyl , organic chemistry , alkyl
In order to synthesize poly‐(fluorinated alkanesulfonamides) a series of model experiments were carried out: (1) reactions of fluorinated alkanesulfonyl fluorides with amines, (2) reactions of fluorinated alkanesulfonyl chloride with amines and (3) reactions of sodium salts of fluorinated alkanesulfonamides with alkyl iodides of fluorinated alkanesulfonic acid esters. Seventeen new fluorinated alkanesulfonamides were prepared in good yields, namely: R F O(CF 2 ) 2 SO 2 NR 1 R 2 (1a‐h), R 1 R 2 NSO 2 R F SO 2 NR 1 R 2 (2a‐h) and [Cl (CF 2 ) 4 O(CF 2 ) 2 SO 2 NH(CH 2 ) 3 ] 2 (3). Reaction of R F SO 2 NH 2 with equivalent amount of NaOCH 3 and methyl iodide was shown to give both the N ‐mono‐ and N,N ‐di‐substituted amides. Consequently the N ‐monosubstituted alkanesulfonamides were chosen as monomers for syntheses of the poly‐(fluorinated alkanesulfonamides) and two new polymers were synthesized. The effect of the condition of the polycondensation on M̄ n of the polymers were discussed and elemental composition, 19 F NMR, IR, M̄ n , Tg, tensile strength, thermal and chemical stabilities of the polymers were measured. Several new perfluoroalkanesulfonyl chlorides CISO 2 R F SO 2 Cl (4a‐c) and fluorinated alkanesulfonic acid esters (6a‐d) were synthesized. However, reaction of CFCl 2 CF 2 O(CF 2 ) 2 SO 2 F with AlCl 3 was found to give Cl 3 CCF 2 O(CF 2 ) 2 SO 2 F (5) instead of the expected sulfonyl chloride.