The structure and the conformation of the two isomeric 3,5-di(4-methoxyphenyl)perhydrocyclopenta[ij]quinolizines 1 and 2 have been determined by a combination of NOE experiments, analysis of vicinal J coupling constants and DFT computations. The two aryl rings were found to exhibit a face to face disposition, and variable temperature NMR spectra allowed the determination of the corresponding rotation barriers, as well as chair to boat and nitrogen inversion processes of the quinolizine rings. The structure and the conformation of the two corresponding ammonium salts 1-H+ and 2-H+ were also obtained in solution by the same techniques: in addition, their solid state structures were determined by X-ray diffraction.
L. Lunazzi, A. Mazzanti, S. Rafi, H.S.P. Rao (2008). Chair to Boat Interconversion and Face to Face Interactions in Isomeric Aryl Substituted Perhydroyclopentaquinolizines. JOURNAL OF ORGANIC CHEMISTRY, 73, 678-688 [10.1021/jo702172u].
Chair to Boat Interconversion and Face to Face Interactions in Isomeric Aryl Substituted Perhydroyclopentaquinolizines
LUNAZZI, LODOVICO;MAZZANTI, ANDREA;
2008
Abstract
The structure and the conformation of the two isomeric 3,5-di(4-methoxyphenyl)perhydrocyclopenta[ij]quinolizines 1 and 2 have been determined by a combination of NOE experiments, analysis of vicinal J coupling constants and DFT computations. The two aryl rings were found to exhibit a face to face disposition, and variable temperature NMR spectra allowed the determination of the corresponding rotation barriers, as well as chair to boat and nitrogen inversion processes of the quinolizine rings. The structure and the conformation of the two corresponding ammonium salts 1-H+ and 2-H+ were also obtained in solution by the same techniques: in addition, their solid state structures were determined by X-ray diffraction.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
