Abstract
1. Dissolution of (1,2),(3,4),(5,6)-tripropanobenzene in HSO3r-SbF5-SO2FCl generated the 1H-(1,2),(3,4),(5,6)-tripropanobenzenonium ion, which is converted by the action of Cl2 to the 1-chloro-(1,2),(3,4),(5,6)-tripropanobenzenonium cation, NMR spectroscopy indicates that these ions undergo a degenerate rearrangement by 1,2-shift of the H and Cl atoms, respectively, at approximately the same rate to C2 and C6. 2. The experimental value of ΔG≠ of the 1,2-chlorine shift in the chlorosubstituted cation is close to that expected on the basis for the reported dependence of ΔG≠Cl on δC+, while the ΔG≠ value for the unsubstituted ion is significantly lower than that expected. This is probably a consequence of a difference in the sensitivity of the σ- and n-type orbitals (H and Cl atoms, respectively) to the effect of orbital orientation.
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