The synthesis of rigid polycyclic structures for the study of diatropic or steric effects of a phenyl ring on CF bond

Yung Yu Chang, I. Ting Ho, Tse Lok Ho*, Wen-Sheng Chung

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

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

Original languageEnglish
Pages (from-to)12790-12794
Number of pages5
JournalJournal of Organic Chemistry
Volume78
Issue number24
DOIs
StatePublished - 20 Dec 2013

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