Derivatives of 5,6,11,12-tetrahydrodibenzo[b,f][1,4]diazocine and 5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocine

Abstract

5,6,11,12-Tetrahydrodibenzo[b,f][1,4]diazocine reacts with paraformaldehyde to give the 5,12-endo-methano-derivative: similar bridged compounds were prepared from aromatic aldehydes, but not ketones. The 5,12-endo-methano-derivative is comparable to Tröger's base in its reactions. The synthesis of N-alkyl-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines and N-alkyl-5,6,11,12-tetrahydrodibenzo[b,f][1,4]diazocines by direct alkylation and by acylation and subsequent reduction has been investigated. An N-amino-and an NN′-diaminoderivative of the [1,5]diazocine were prepared.