A bisdehydro[14]annuleno[c]furan and a tetrakisdehydro[14]annuleno[14]annulene have been synthesized; their properties and effects of annelation on annulene rings are discussed on the basis of 1H NMR and electronic spectra. Attempts to synthesize the related [14]annuleno[16]annuleno[14]annulene are also described.