Static and dynamic stereochemistry of the conformational atropisomers of tetra(o-tolyl)benzene.
[graph: see text] Whereas only one atropisomer of 1,2,4,5-tetra(o-tolyl)benzene was observed by X-ray diffraction in the solid, five conformational atropisomers were detected by low-temperature NMR in solution. Their structures were assigned by a combination of NOE experiments, solvent effect, and ab initio calculations. Variable temperature dynamic NMR and bidimensional EXSY experiments allowed the barrier for the interconversion of these atropisomers to be determined (deltaG(double dagger) = 15.3 kcal mol(-1)).
Lunazzi
Lodovico
L
Department of Organic Chemistry A. Mangini, University of Bologna, viale Risorgimento 4, Bologna I-40136, Italy.
Mazzanti
Andrea
A
Minzoni
Mirko
M