Add time:08/10/2019 Source:sciencedirect.com
A superacidic polymer Nafion protonates ferrocenylacetylene (1) in sc−CO2 (35 °C, 9 MPa) to from the α-ferrocenylvinyl cation, FcC+=CH2 (2, Fc = ferrocenyl). Carbocation 2 in situ alkenylates dimethyl sulfide (25 MPa) or 1,4-dithiane (35 MPa) to give 1-ferrocenylvinyl sulfonium salts isolated as the tetrafluoroborates: [Me2S+C(Fc)=CH2]BF4− (3, 85%), cis- [R2S+C(Fc)=CH2]BF4− (R2 = CH2CH2SCH2CH2) (4, 31%) and trans-[R2S+CH = CH(Fc)]BF4− (5, 91%). Salt 5 is the isomer of compound 4 resulting from the 1,4-dithiane ring shift from α- to β- position to the Fc group. Salt 5 undergoes S+–C bond scission on the action of HN(i-Pr)2 affording the neutral diene trans-FcCH = CHSCH2CH2SCH = CH2 (6, 89%). Complexes 4-6 were fully characterized by the NMR spectra data. The molecular structures of 4 and 5 were elucidated by X-ray study.
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