Title: The Synthesis of Rigid Polycyclic Structures for the Study of Diatropic or Steric Effects of a Phenyl Ring on CF Bond
Authors: Chang, Yung-Yu
Ho, I-Ting
Ho, Tse-Lok
Chung, Wen-Sheng
Department of Applied Chemistry
Issue Date: 20-Dec-2013
Abstract: Polycyclic compounds 1a-c were synthesized to study the diatropic effects of a flanking phenyl ring on nearby CH and CF bonds. F-19 NMR spectra of 1b and 1c were strongly deshielded compared with those of the ring-opened compounds 3b, 7b, and 7c. DMol3 calculations on 1a-c provided quantitative bond lengths and torsional angles to support the conclusion that the downfield shifts in the F-19 NMR spectra are mainly due to steric interactions between the CF bonds and the pi clouds of the phenyl ring(s).
URI: http://dx.doi.org/10.1021/jo402154f
ISSN: 0022-3263
DOI: 10.1021/jo402154f
Volume: 78
Issue: 24
Begin Page: 12790
End Page: 12794
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