Journal of Organic Chemistry p. 1847 - 1850 (1987)
Update date:2022-09-26
Topics:
Bartlett, Paul D.
Ravenscroft, Michael D.
Roof, Antonius A. M.
In superacid media, anti-sesquinorbornene (2) is protonated to yield the directly related carbocation 2+ at -78 deg C.On raising the temperature the cation rearranges irreversibly with ring opening to the 1-(2-norbornyl)-2-cyclopentenyl allylic cation 3+.This rearrangement does not occur with syn-sesquinorbornene, within the temperature range studied, but is observed in the syn isomer 7 whose double bond is not shared between the norbornene ring systems.These observations permit the formulation of a general mechanism for the formation of the allylic cation.
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