HALOGENATION OF 1,6-DIAZAPHENALENE. THEORETICAL AND EXPERIMENTAL RESULTS

Bromination of 1,6-diazaphenalene 1 yields a mixture of mono-, di-, and tri-bromo derivatives, while bromination of the conjugate acid 2 provides the 7-bromo isomer 7 in 81% yield. Charge densities and localization energies have been calculated, and are found to be in agreement with the orientation pattern observed during electrophilic substitution. These observations have been employed to develop several routes to 7-substituted 1,6-diazaphenalenes.