Synthesis of 7, 8: 13, 14-dibenzo-2, 9, 11-trisdehydro [16] annulene-1, 4-dione is described. Attempts to prepare diaza [18] annulene derivatives by ring expansion of the dibenz [16] annulenedione and its dimethyl analog are also described. Examination of 1 H NMR spectra indicates that the dibenz [16] annulenedione shows no ring current effect.