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Paper | Special issue | Vol 40, No. 2, 1995, pp.577-582
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S39
Photoinduced Reactions of Benzo[b]phenazine

Elisa Fasani*, Mariella Mella, and Angelo Albini

*Dipartiment di Chimica Organica, Università di Pavia, V.le Taramelli 10, 27100 Pavia, Italy


While the photochemistry of azines is generally dominated by hydrogen abstraction from nΠ* states, benzo[b]phenazine has low-lying ΠΠ* states and undergoes both [4+4] dimerization (the main product is the less hindered biplanemer (2), but a small amount of the alternative dimer (3) is also formed) and self-sensitized photo-oxygenation to yield the endo-peroxide (5) (better obtained with an added sensitizer). Compound (5) undergoes decomposition by O-O bond cleavage to yield the quinone (4) and the diol (6).