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The reactions of tetrafluoroethylene oligomers: V. The reactions of perfluoro‐3,4‐dimethyl‐4‐ethylhexene‐(2) with thionucleophiles and the chemical transformations of reaction products
Author(s) -
Chen LiFo,
Wang JunHuan,
Hu ChangMing
Publication year - 1985
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.19850030309
Subject(s) - chemistry , nucleophile , dimethylamine , tetrafluoroethylene , dimethyl ether , yield (engineering) , ether , medicinal chemistry , intramolecular force , olefin fiber , organic chemistry , methanol , catalysis , materials science , copolymer , metallurgy , polymer
The reactions of perfluoro‐3,4‐dimethyl‐4‐ethylhexene‐(2) (1) with s ‐nucleophiles such as benzylthiol, allylthiol, phenylthiol and the chemical transformations of these reaction products were reported. 1 reacted with S ‐nucleophiles to give four types of isomeric products. At −30∼ −60°C, in ether, kinetically controlled product 2 (a, b, c) were formed. Compound 2 might be converted directly into the thermodynamically stable products 3 (a, b,) in DMF‐KF at r.t., At 100°C, 2 was converted to 4 (a, b, c) via intramolecular rearrangement. In KF‐DMF at r.t., 4 was isomerized to 5 (a, b, c). 2a also reacted with another mole of thiol to give the corresponding disulfide 6 and hydrogen‐containing olefin 7a as well as the disubstituted product 8a in DMF, but only give 3a and 9a in ether‐Et 3 N. The reaction of 2a with methyl alcohol gave only a small amounts of 3a and 10a. The reaction of 2b with dimethylamine was complex and 3b and 11 were obtained in low yield.