Journal of Fluorine Chemistry p. 197 - 204 (1995)
Update date:2022-08-03
Topics:
Ono, Taizo
Yamanouchi, Kouichi
Fernandez, Richard E.
Scherer, Kirby V.
Liquid-phase photofluorination (LPPF) of 2-phenyl-2-methoxyhexafluoropropane 1 gave the desired F-2-cyclohexyl-2-methoxypropane, 2, in 21percent yield.An unusual rearranged product, F-2-cyclohexylmethyl isopropyl ether, 4, and a degradation product, F-2-cyclohexylpropane, 3, were also produced in 10 and 20percent yields, respectively.A plausible reaction mechanism for the formation of the rearranged product 4 was presented.The Cl-containing ethers with cyclic structures, 2-chlorohexafluorocyclopentenyl cyclopentyl ether, and 2-chlorohexafluorocyclopentenyl 2,2,3,3,4,4,5,5-octafluoro-n-pentyl ether were also perfluorinated by the LPPF method to give the corresponding Cl-containing F-ethers in fair yields.The total retention of the chlorine atom through perfluorination and the ability to have a benzene substituent on the substrate are beneficial features of this novel perfluorinating method. - Keywords: Liquid-phase photofluorination; Perfluorocycloalkyl ethers; GC-MS; 19F-NMR
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