Polyfluorocycloalkenes. Part XVII. Further preparations of alkoxy-nonafluorocyclohexenes and their pyrolyses to polyfluorocyclohEx-2-enones

Add time:07/18/2019    Source:sciencedirect.com

Reactions between decafluorocyclohexene and substituted ethanols (HOCH2CH2X: X = Cl, Br, I, and OMe) gave, in each case, a mixture of the corresponding 1- and 3-alkoxy-nonafluorocyclohexene (roughly 3:1). Pyrolysis of the 1-(2-methoxyethoxide) over glass or alumina at 520°C gave octafluorocyclohex-2-enone. This was obtained also in good yield by pyrolysis of the known 1-ethoxy- and 1-(2-acetoxyethoxy)- analogues. From the other 1-alkoxides the same enone was formed, but accompanied by other products: from the 1-(2-bromoethoxide), nonafluorocyclohex-1-enyl vinyl ether and 3-bromoheptafluorocyclohex-2-enone; from the 1-(2-iodoethoxide), the vinyl ether and 2-chloroheptafluorocyclohex-2-enone; from the 1-(2-iodoethoxide) at 395°C, 6,6,7,7,8,8,9,9-octafluoro-2-oxabicyclo[4,3,0]nona-1(5),3-diene. Pyrolyses at lower temperatures gave much unreacted 1-alkoxides, but no rearrangement to 3-alkoxides was detected. In contrast, the 3-ethoxy- and 3-(1-bromoethoxy)-isomers decomposed to a greater extent at 390°C, to give the octafluoroenone, but, besides unreacted starting materials, some isomeric 1-alkoxide was present in each case. Reaction of octafluorocyclohex-2-enone with chlorides and bromides gave the respective 3-chloro- and 3-bromo-2-enones, whilst with base, a haloform cleavage took place within the conjugated system to give cis-6H-octafluorohex-5-enoic acid.

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