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

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

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	12790-12794
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	78
Issue number	24
DOIs	https://doi.org/10.1021/jo402154f
State	Published - 20 Dec 2013

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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).",

author = "Chang, {Yung Yu} and Ho, {I. Ting} and Ho, {Tse Lok} and Wen-Sheng Chung",

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T1 - The synthesis of rigid polycyclic structures for the study of diatropic or steric effects of a phenyl ring on CF bond

AU - Chang, Yung Yu

AU - Ho, I. Ting

AU - Ho, Tse Lok

AU - Chung, Wen-Sheng

PY - 2013/12/20

Y1 - 2013/12/20

N2 - 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).

AB - 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).

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U2 - 10.1021/jo402154f

DO - 10.1021/jo402154f

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EP - 12794

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 24

ER -

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

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