Aromatic 4-tetrahydropyranyl and 4-quinuclidinyl cations. Linking Prins with Cope and Grob.
The chair 4-tetrahydropyranyl cation and the 4-quinuclidinyl cation are shown to be energy minima and to be delocalized, with exceptionally long CH2CH2 bonds, according to B3LYP/6-31G* calculations; the implications for Prins cyclizations, Cope rearrangements, and Grob fragmentations are discussed.
Alder
Roger W
RW
School of Chemistry, University of Bristol, Bristol, United Kingdom BS8 1TS. rog.alder@bris.ac.uk
Harvey
Jeremy N
JN
Oakley
Mark T
MT