Unusual open chain quinolinyl peroxol and its alcohol counterpart obtained through a modified Skraup-Doebner-Von Miller quinoline synthesis theoretical studies and complete (1) H- and (13) C-NMR assignments

Unusual open chain quinolinyl peroxol and its alcohol counterpart obtained through a modified Skraup-Doebner-Von Miller quinoline synthesis : theoretical studies and complete (1) H- and (13) C-NMR assignments

Copyright © 2012 John Wiley & Sons, Ltd.

Bibliographische Detailangaben
Veröffentlicht in:Magnetic resonance in chemistry : MRC. - 1985. - 50(2012), 1 vom: 19. Jan., Seite 68-73
1. Verfasser: Fotie, Jean (VerfasserIn)
Weitere Verfasser: Kemami Wangun, Hilaire V, Dreux, Katelyn, Sommerfeld, Thomas, Pittman, Jacob
Format: Online-Aufsatz
Sprache:English
Veröffentlicht: 2012
Zugriff auf das übergeordnete Werk:Magnetic resonance in chemistry : MRC
Schlagworte:Journal Article Alcohols Carbon Isotopes Peroxides Protons Quinolines quinoline E66400VT9R
Beschreibung
Zusammenfassung:Copyright © 2012 John Wiley & Sons, Ltd.
Because of their extreme instability, it is generally difficult to synthesize and fully characterize open chain peroxides, also known as peroxols. In our attempt to investigate the mechanism of the Skraup-Doebner-Von Miller quinoline synthesis, we were able to obtain an unusual open chain peroxy-quinoline, namely, 4-(8-ethoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4-yl)butane-1-peroxol (1), and its alcohol counterpart, namely 4-(8-ethoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4-yl)butan-1-ol (2) obtained as a side product during the same reaction. Although structurally similar, these two compounds appeared to display some very distinct physical and spectroscopic characteristics. This work reports detailed NMR studies and full (1) H and (13)  C NMR assignments for these two compounds. These assignments are based upon the analysis of the NMR spectra of these compounds including (1) H, (13)  C, COSY, gHSQC and gHMBC. The effect of the peroxide functional group on the chemical shift of neighboring carbons and protons was also investigated by comparing the NMR data of these two compounds. Furthermore, the effects of potential hydrogen bondings in 1, 2, and possible 1-1 dimer, 2-2 dimer and in prototypical model systems, as well as the stability of these compounds, were investigated computationally. The computed dissociation energies and NMR data support the interpretation of the experimental data
Beschreibung:Date Completed 23.08.2012
Date Revised 15.11.2012
published: Print-Electronic
Citation Status MEDLINE
ISSN:1097-458X
DOI:10.1002/mrc.3791