Journal of the Chemical Society - Faraday Transactions p. 3145 - 3152 (1992)
Update date:2022-08-30
Topics:
Hamanoue, Kumao
Nakayama, Toshihiro
Kajiwara, Kanji
Yamanaka, Shigenobu
Ushida, Kiminori
From measurements of phosphorescence and triplet-triplet absorption spectra of the lowest excited triplet ??* state of 9-nitroanthracene (NA) together with the absorption spectrum of 9-anthryloxy radical, it is concluded that photolysis of 9-nitroanthracene gives rise to the nitro -> nitrite rearrangement for a higher excited triplet state of n?* character, followed by the cleavage of 9-anthryl nitrite to 9-anthryloxy radical and nitrogen(II) oxide, yielding 9-anthrol (and anthrone), 10,10'-bianthrone and 9-nitrosoanthrone in ethanol; and 10,10'-bianthrone and 9-nitrosoanthrone in benzene.Hence, the primary process in the photochemical reaction of NA is essentially identical with those of 9-benzoyl-10-nitroanthracene and 9-cyano-10-nitroanthracene except that no 10,10'-bianthrone derivatives are formed.
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