86556-81-2Relevant academic research and scientific papers
Vinyl ether compound, process for producing the same and copolymer containing the same
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, (2008/06/13)
A novel bifunctional vinyl ether compound having an aromatic ring, represented by the following general formula: STR1 where X is a halogen atom and n is an integer of 1 to 5, effective as a copolymer component for fluorine-containing elastomers is produced by adding a chlorine atom or a bromine atom (Y) to CF2 =CFO(CF2)nCOOR, where R is a lower alkyl group, then subjecting the resulting CF2 YCFYO(CF2)nCOOR to hydrolysis and acid chloridation, followed by reaction with monohalogenobenzene, reaction with SF4 to convert --CO-- to --CF2 --, and dechlorination or debromination, or by subjecting CF2 =CFO (CF2)nCOOR to hydrolysis and acid chloridation, followed by reaction with monohalogenobenzene and reaction with SF, to convert --CO-- to --CF2 --.
The synthesis of phosphonate ester containing fluorinated vinyl ethers
Pedersen, Scot D.,Qiu, Weiming,Qiu, Zai-Ming,Kotov, Stefan V.,Burton, Donald J.
, p. 8024 - 8031 (2007/10/03)
Three novel perfluorovinyl ethers containing phosphonate ester groups, diethyl 1,1,2,2,3,3,5,6,6-nonafluoro-4-oxa-5-hexenylphosphonate, (EtO)2P(O)(CF2)3OCF=CF2 (1), diethyl 1,1,2,2,4,5,5-heptafluoro-3-oxa-4-pentenylphosphonate, (EtO)2P(O)(CF2)2OCF=CF2 (2), and diethyl 1,1,2,2,4,5,5,7,8,8-decafluoro-4-trifluoromethyl-3,6-dioxa-7-octenylph osphonate, CF2=CFOCF2CF(CF3)O(CF2)2P(O)(OEt)2 (3), have been synthesized. Perfluorovinyl ethers 1 and 2 were synthesized from methyl 4-trifluoroethenoxy-2,2,3,3,4,4-hexafluorobutanoate and methyl 3-trifluoroethenoxy-2,2,3,3-tetrafluoropropanoate, respectively, while perfluorovinyl ether 3 was synthesized either from 5-trifluoroethenoxy-4-trifluoromethyl-3-oxa-1,1,2,2,4,5,5-heptafluorop entylsulfonyl fluoride or methyl 6-trifluoroethenoxy-5-trifluoromethyl-4-oxa-2,2,3,3,5,6,6-heptafluoroh exanoate. The carboxylate esters were converted to the corresponding fluoroalkyl iodides via a free-radical iododecarboxylation. The sulfonyl fluoride was converted to its corresponding fluoroalkyl iodide via iododesulfination. The intermediate iodides were found to be useful precursors for the incorporation of the phosphonic ester groups via a photoreaction with tetraethyl pyrophosphite to produce diethyl fluorophosphonites. The diethyl fluorophosphonites were oxidized to the desired phosphonates, 1, 2, and 3, utilizing hydrogen peroxide as the oxidant. Moderate to good overall yields of perfluorovinyl ethers 1-3 have been achieved.
