Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Comparing the Stability of Geometrically rigid Tricyclopropyl Carbinyl Cations by $^{19}$F NMR Spectroscopy

  • Shin, Jung-Hyu (Department of Chemistry, Seoul National University) ;
  • Kim, Kyong-Tae (Department of Chemistry, Seoul National University) ;
  • Shin, Hun-Woo (Department of Chemistry, Seoul National University)
  • Published : 1987.06.20
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Abstract

The relative stability as function of geometry in the rigid tricyclopropylcarbinyl cations with varied bond angle (${\alpha}$) between the plane of cyclopropane ring and the bond connecting cyclopropane ring to cationic carbon was examined by $^{19}F$ nmr spectroscopy. 7-p-Fluorophenyltricyclo[2.2.2.$0^{2,6}$]octan-7-yl(4) and 8-p-fluorophenyltricyclo[3.2.2.$0^{2,7}$]nonan-8-yl cation (8) were generated from corresponding tertiary alcohols under stable ion conditions, and their $^{19}F$ chemical shifts were compared with those of model compounds such as 7-nortricyclyl cation (3) and tricyclo[3.3.1.$0^{2,7}$]octan-8-yl cation (7). Consequently, it is concluded that the varied orientation of bond angle (${\alpha}$) within in the bisected conformation does not affect degree of the charge delocalization into cyclopropane ring.

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