ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 29, Number 3
JKCSEZ 29(3)
June 20, 1985 

The relative stability as a function of geometry in rigid cyclopropylcarbinyl cations was examined by 19F-nmr spectroscopy. 8-p-Fluorophenyl-tricyclo[3.3.1.02,7]octane-8-yl-(Ⅰ), 9-p-fluorophenyl-tricyclo[3.3.1.02,8]nonane-9-yl (Ⅱ), and 10-p-fluorophenyl-tricyclo[4.3.1.02,9]decane-10-yl cation(Ⅲ) were prepared from the corresponding carbinols in FSO3H-SO2ClF solution at -120℃. 19F-nmr data indicate that the symmetrical bisected geometry of cyclopropane ring for σ-conjugation is a very impotant factor in charge delocalization. However, varied orientation of the bond angle θ within the bisected conformation does not affect the charge delocalization into the cyclopropane ring.