ATROPISOMERIC AND CONFORMATIONAL PROPERTIES OF 6N-BENZOYL- AND 6N-p-TOSYL-1,6-BENZODIAZOCINES: COMPARISON WITH THOSE OF 1,5-BENZODIAZEPINES

摘要

The atropisomeric and conformational properties of the eight-membered 1,6-benzodiazocines (2) with 6N-benzoyl (A) and 6N-p-tosyl (B) groups were examined by comparing them with those of the seven-membered 1,5-benzodiazepine congeners (1) (A, B). The conformation (orientation) of the benzene ring in the benzoyl and tosyl groups differed depending on the ring size (7/8) and N-substituent (-CO-/-SO2-). The activation free-energy barrier to rotation of the axes in N-p-tosyl derivatives (B) was shown to be much higher than those of the benzoyl derivatives (A).