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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 8, Number 3
March 20, 1987 

Comparing the Stability of Geometrically rigid Tricyclopropyl Carbinyl Cations by 19F NMR Spectroscopy
Jung-Hyu Shin*, Kyongtae Kim, Hun-Woo Shin
The relative stability as function of geometry in the rigid tricyclopropylcarbinyl cations with varied bond angle (α) between the plane of cyclopropane ring and the bond connecting cyclopropane ring to cationic carbon was examined by 19F nmr spectroscopy. 7-p-Fluorophenyltricyclo[,6]octan-7-yl(4) and 8-p-fluorophenyltricyclo[,7]nonan-8-yl cation (8) were generated from corresponding tertiary alcohols under stable ion conditions, and their 19F chemical shifts were compared with those of model compounds such as 7-nortricyclyl cation (3) and tricyclo[,7]octan-8-yl cation (7). Consequently, it is concluded that the varied orientation of bond angle (α) within in the bisected conformation does not affect degree of the charge delocalization into cyclopropane ring.
144 - 146
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