8-phenyl-10,10a-dihydropyrido
Base treatment of the pyridinium bromides 11a-e gives rise to the formation of the dihydropyridoazepines 14a-e as the only monomolecular products. The reaction takes place by initial deprotonation to the ylides 12, which undergo 8pi-electrocyclization affording the seven-membered-ring systems; no products of a dipolar 6pi-cyclization were detected. On the basis of quantum mechanical calculations a rationalization of the periselectivity of the electrocyclization process is given.
Marx
K
Institut fur Organische Chemie und Biochemie der Universitat Freiburg, Germany.
Eberbach
W