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Fluoro-olefin Chemistry. Part 16. Reaction of Hexafluoropropene with n-Butane and n-Pentane
Davies, Terry,Haszeldine, Robert N.,Rowland, Ronald,Tipping, Anthony E.
, p. 109 - 114 (2007/10/02)
Thermal reaction of hexafluoropropene with n-butane at ca. 300 deg C gives 1:1 and 2:1 adducts n (11), Bus (12), and CHMeCH2CH2CF2CHFCF3 (14)>, together with lower alkane adducts HR (R = Me, Et, Prn, and Pri) and 1,1,1,2,3,3-hexafluoropropane (4).The 1:1 adducts are precursors of the 2:1 adducts and the lower alkane adducts, and the structures of the isolated 2:1 adducts indicate that C-H bonds α- and β- to the fluoroalkyl group in the 1:1 adducts are deactivated towards hydrogen abstraction.It is proposed that the 1:1 and 2:1 adducts arise by a radical-chain mechanism initiated by hydrogen abstraction from n-butane and the 1:1 adducts, respectively, and that the lower alkane adducts are formed via interaction between the 1:1 adducts and excited hexafluoropropene resulting in C-C bond fission.The photochemical and peroxide-initiated reaction give much higher yields of 1:1 and 2:1 adducts at the expense of the lower alkane adducts.Analogous products are formed in the thermal reaction with n-pentane n (16), CHEt2 (17), CHMeCH2CHMeCF2CHFCF3 (18), and CHMe(CH2)3CF2CHFCF3 (19)>, but, surprisingly, 2:1 adducts formed via hydrogen abstraction from the γ-C-H bonds (CH3) of the 1:1 adduct (17) are absent.
