104330-35-0Relevant academic research and scientific papers
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.
