85131-87-9Relevant academic research and scientific papers
ADDITION OF 1,2-DIBROMO-1-CHLOROTRIFLUOROETHANE TO CHLOROTRIFLUOROETHYLENE INDUCED BY UV-RADIATION. SYNTHESIS OF PERFLUORO-1,3-BUTADIENE AND PERFLUORO-1,3,5-HEXATRIENE
Dedek, V.,Chvatal, Z.
, p. 363 - 380 (2007/10/02)
Photochemically initiated reaction of 1,2-dibromo-1-chlorotrifluoroethane (II) with chlorotrifluoroethylene (I) gave 38percent 1,4-dibromo-2,3-dichlorohexafluorobutane (III) and 19percent 1,6-dibromo-2,3,5-trichlorononafluorohexane (IV) in addition to the higher telomers.Dehalogenations of III and IV yielded perfluoro-1,3-butadiene (VI) and perfluoro-1,3,5-hexatriene (VIII) with 3-chlorononafluoro-1,5-hexadiene (VII), respectively.Photochemical reduction of butane III with 2-propanol resulted in a preferential reduction of C-Br bonds, and from 2,3-dichloro-1,1,2,3,4,4-hexafluorobutane (IX) thus formed, esters of difluoroacetic acid were prepared by dehalogenation of IX and subsequent oxidation and esterification of the product.The photochemical reduction of hexane IV gave a mixture of 79percent trichlorononafluorohexane XII and 21percent dichlorononafluorohexane XIII.The mechanism of formation of the unusual products of the title addition reaction is discussed.
ADDITION OF PRIMARY ALCOHOLS TO 3-CHLORONONAFLUORO-1,5-HEXADIENE AND PERFLUORO-1,3,5-HEXATRIENE
Dedek, Vaclav,Linhart, Igor,Kovac, Milan
, p. 1714 - 1726 (2007/10/02)
Sodium alkoxide-catalyzed addition of methanol, ethanol and propanol to 3-chlorononafluoro-1,5-hexadiene (I) proceeds at temperatures -35 deg C to 8 deg C with allyl rearrangement, affording 1,6-dialkoxy-1,1,2,3,4,4,5,6,6-octafluoro-2,4-hexadiene (V) as the principal product, along with 1,6-dialkoxy-1,2,3,3,4,5,6,6-octafluoro-1,5-diene (VI) and trans-1,6-dialkoxy-1,1,2,3,4,4,5,6,6-nonafluoro-2-hexene (VII).The ethers Va-Vc consist of the cis,trans- and trans,trans-isomers in about 3:1 ratio, whereas the ethers VIa-VIc have trans,trans-configuration.Ethers Vc and VIc react with concentrated sulfuric acid to give dipropyl 2,3,4,5-tetrafluoro-2,4-hexadienedioate (IX) and dipropyl 2,3,4,4,5-pentafluoro-2-hexenedioate (X), respectively, whereas the ether VIIc affords a mixture of propyl 6-propyloxy-2,3,4,4,5,6-heptafluoro-2-hexenoate (XI) and ester X.Addition of methanol to perfluoro-1,3,5-hexatriene (II) affords 1,1,2,3,4,5,6,6-octafluoro-1,6-dimethoxy-3-hexene (XIII) as the principal product.
