DIAZABICYCLOALKANES WITH NITROGEN ATOMS IN THE NODAL POSITIONS. 10. INTRAMOLECULAR CYCLIZATION OF β-BROMOETHYL-AND γ-BROMOPROPYL-N,N'-ALKYLENE-o-PHENYLENEDIAMINES

Article abstract of DOI:10.1007/BF00514469

The overall scheme of the intramolecular cyclization of bromoalkyl derivatives of N,N'-alkylene-o-phenylenediamines in HBr was established, and the rates of the individual steps of this complex process were estimated.It is shown that N-(β-bromoethyl)-N,N'-trimethylene-o-phenylenediamine undergoes virtually irreversible cyclization at a high rate to give benzo-1,5-diazabicyclo<3.2.2>-nonene in significant yield, while the cyclization of N-(γ-bromopropyl)-1,2,3,4-tetrahydroquinoxaline proceeds at commensurable rates via two pathways, viz., C- and N-alkylation.This makes it impossible to use the latter reaction to obtain benzo-1,5-diazabicyclo<3.2.2>nonene in high yield.