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Paper | Regular issue | Vol 27, No. 4, 1988, pp.933-942
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4441
Characterization and Photochemical Reactivity of Triphenodioxazine N-Oxides

Adele Bolognese, Giulia Scherillo, and Angelo Albini

*Dipartimento di Chimica Organica e Biologica, Università di Napoli "Federico II", Via Mezzocannone 16, I-80134 Napoli, Italy


N-Oxidation of triphenodioxazine (1) by m-chloroperbenzoic acid in choroform yields the corresponding 7-oxide (2) and 7,14-dioxide (3). Their coloured solutions in organic solvents are very sensitive to light. Irradiation in the visible in various solvents leads to deoxygenation. The photoreaction of compound 3 in chloroform yields also N (7)-(6’-triphenodiaxazinyl)-3,7-dihydrotriphenodioxazin-3-one (4) and the corresponding N-oxides 5 and 6, as well as 1-, 3- and 13-chlorotriphenodioxazine 7-oxides (7-9). The nature of the excited state of these N-oxides is discussed and a mechanism for product formation is proposed.