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- W2073898687 abstract "The free-radical addition of 2-(perfluoroalkyl)ethanethiols (RFCH2CH2SH) to alkenes,cycloalkenes, alkadienes and alkynes has been studied to determine: (1) the mode ofreaction, i.e. the stereochemistry, regiochemistry and any skeletal changes; (2) the relativereactivity towards unsaturates of differing structures and classes as affected by the presenceof the RF group; and (3) the influence of the reaction conditions on the rate of additionor selectivity for different products. Adducts from 2-(F-hexyl)ethane thiol (1) and alkeneshave been obtained in high yield, but containing small amounts of regio isomers. Forexample, compound 1 with 1-heptene gave 1-[2-(F-hexyl)ethanethio]heptane (3, 96%yield) as well as 2-[2-(F-hexyl)ethanethio]heptane (4, 0.61%) and 3-[2-(F-hexyl)ethanethio]heptane(5, 2.22%). 1,6-Hexadiene and 1,7-octadiene gave chieflylinear adducts, i.e. RFCH2CH2S(CH2)nCHCH2 (7, n = 4; or 12, n = 6, respectively) andRFCH2CH2S(CH2)nSCH2CH2RF (8, n = 6; or 14, n = 8, respectively). A small amount (2–3%)of cis- and trans-1-methyl-[2-(F-hexyl)ethanethiomethyl]cyclohexane (13) isomers werepresent in 12. Compound 1 with 1,6-heptadiene gave 7-[2-(F-hexyl)ethanethio]-1-heptene(9), the bis adduct, 1,7-bis-[2-(F-hexyl)ethanethio]heptane (11) and the cyclic adducts,cis- and trans-1-methyl-2-[2-(F-hexyl)-ethanethio]methylcyclopentane (10). The relativeamounts of cyclic isomers depended on the reactant ratio. Compound 1 added readilywith free-radical initiation to vinyl monomers such as styrene and vinyl acetate, and tophenyl acetylene, propargyl acetate and ethyl propynoate. These new addition productsare useful as models for further study." @default.
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- W2073898687 date "1993-06-01" @default.
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- W2073898687 title "Free-radical addition of 2-(perfluoroalkyl)ethanethiols to alkenes, alkadienes, cycloalkenes, alkynes and vinyl monomers" @default.
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- W2073898687 doi "https://doi.org/10.1016/s0022-1139(00)80097-4" @default.
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