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

doi:10.1021/jo402154f

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

J Org Chem. 2013 Dec 20;78(24):12790-4. doi: 10.1021/jo402154f. Epub 2013 Dec 10.

Authors

Yung-Yu Chang¹, I-Ting Ho, Tse-Lok Ho, Wen-Sheng Chung

Affiliation

¹ Department of Applied Chemistry, National Chiao-Tung University , Hsinchu 30050, Taiwan ROC.

PMID: 24325615
DOI: 10.1021/jo402154f

Abstract

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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Polycyclic Compounds / chemical synthesis*
Polycyclic Compounds / chemistry

Substances

Polycyclic Compounds