Stereodynamics and conformational chirality of the atropisomers of ditolyl anthrones and anthraquinone.
Syn and anti conformers in similar proportions were observed at ambient temperature for the title compounds. The conformational assignment of the two anthrones was obtained by the observation of different multiplicity of the methylene NMR signals, whereas that of the anthraquinone derivative was determined by NOE experiments. The anti-to-syn interconversion barriers were obtained by line-shape simulation of the temperature-dependent NMR spectra, and by saturation transfer experiments. In one case the X-ray diffraction indicated that the syn is the only structure observed in the crystals.
Department of Organic Chemistry A. Mangini, University of Bologna, Viale Risorgimento 4, Bologna 40136, Italy.
Lodovico
L
Lunazzi
Michele
M
Mancinelli
Andrea
A
Mazzanti
D000873:Anthracenes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013696:Temperature
D000873:Anthracenes