Products of the photolyses of the naphthylbenzotriazoles (3) include the red cyclo-octa[def]carbazoles (4), a new ring system formed by unusual cyclisation onto the naphthalene 8a-position; from its 1H n.m.r. spectrum and chemical reactivity, (4) is considered to have antiaromatic paratropic character, associated with the 16π-electron periphery (12), comparable to the isoelectronic fluorenyl anion derived from (1).
J. J. Kulagowski, G. Mitchell, C. J. Moody and C. W. Rees, J. Chem. Soc., Chem. Commun., 1985, 652 DOI: 10.1039/C39850000652
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