107082-01-9Relevant academic research and scientific papers
Ring-Opening Rearrangements of Sesquinorbornyl Cations
Bartlett, Paul D.,Ravenscroft, Michael D.,Roof, Antonius A. M.
, p. 1847 - 1850 (2007/10/02)
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.
