Journal of Organic Chemistry p. 1478 - 1482 (1985)
Update date:2022-08-18
Topics:
Hojo, Masaru
Ichi, Tadaaki
Shibato, Kishio
9,9-Bis(methylthio)-1-isopropenylfluorene (3) and the corresponding alcohol 2 generate a carbocation 1 in trifluoroacetic acid solution at room temperature.This ion is sufficiently stable to be observed spectroscopically in this solution.A stable crystalline hexachloroantimonate of 1 was isolated.In trifluoroacetic acid-d at room temperature, the two C+-methyl groups of 1 undergo H-D isotopic exchange to give the corresponding hexadeuterio cation.On the basis of electronic and 1H NMR spectroscopic data at temperatures from 40 to -60 deg C, it is concluded that ion 1 is not a sulfonium species but exists as a carbocation stabilized by electrons from the two neighboring sulfur atoms.Carbon-13 NMR data show that the positive charge is extensively delocalized over the neighboring sulfur atoms, with small amount remaining on the carbon atom.The possibility is suggested that 1 is a pentacoordinated carbon species that resembles the transition states in SN2 displacements.
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