The Synthesis of Rigid Polycyclic Structures for the Study of Diatropic or Steric Effects of a Phenyl Ring on CF Bond | Zendy

YungYu Chang | Zendy; ITing Ho | Zendy; TseLok Ho | Zendy; WenSheng Chung | Zendy

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The Synthesis of Rigid Polycyclic Structures for the Study of Diatropic or Steric Effects of a Phenyl Ring on CF Bond

Author(s) -

YungYu Chang,

ITing Ho,

TseLok Ho,

WenSheng Chung

Publication year - 2013

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo402154f

Subject(s) - chemistry , steric effects , ring (chemistry) , stereochemistry , computational chemistry , organic chemistry

Polycyclic compounds 1a-c were synthesized to study the diatropic effects of a flanking phenyl ring on nearby CH and CF bonds. (19)F 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 (19)F NMR spectra are mainly due to steric interactions between the CF bonds and the π clouds of the phenyl ring(s).

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