1964 年 84 巻 7 号 p. 656-663
Condensation of 1, 2, 3, 4, 5, 6-hexahydrobenzo[b][1, 5]diazocine (IV) with formaldehyde, benzaldehyde, or acetaldehyde afforded respectively 3, 4-dihydro-2H, 6H-1, 5-methanobenzo[b][1, 5]diazocine (Va), its 11-phenyl (Vb), and 11-methyl derivatives (Vc). Reaction of 2, 3, 45, -tetrahydro-1H-benzo[e][1, 4]diazecine (VII) with formaldehyde or benzaldehyde afforded 2, 3-dihydro-5H-1, 4-methanobenzo[e][1, 4]diazepine (VIIIa) and its 10-phenyl derivative (VIIIb).
From their nuclear magnetic resonance spectra and Dreiding models, it was assumed that the substituent at the 11-position of Vb and Vc had configuration of A-formula, and the phenyl group at the 10-position of VIIIb had configuration of B-formula.
Whereas the phenyl derivatives (Vb and VIIIb) were hydrolyzed to IV or VII and benzaldehyde by merely being dissolved in 0.1N hydrochloric acid, Va, Vc, and VIIIa were found to be not hydrolyzed by this acidity.