Journal of the Chemical Society. Perkin transactions II p. 1709 - 1714 (1990)
Update date:2022-07-29
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Yamaoka, Tsuguo
Adachi, Hiroshi
Matsumoto, Kazuo
Watanabe, Hiroo
Shirosaki, Tsutomu
While o-nitrobenzyl aromatic sulphonates are known to photodissociate via an intramolecular rearrangement, photodissociation of p-nitrobenzyl aromatic sulphonates has not been reported.In this study, we report that p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulphonate is photochemically dissociated to give 9,10-dimethoxyanthracene-2-sulphonic acid, 9,10-dimethoxy-2-(p-nitrobenzyl)-anthracene, and p,p'-dinitrobibenzyl.The dissociation is considered to proceed via an intramolecular electron transfer from the 9,10-dimethoxyanthracene moiety to the p-nitrobenzyl moiety.The quantum yield of the photodissociation in acetonitrile is 0.11 and the spectral response extends to 450 nm.The quantum yield is much higher than those of o-nitrobenzyl esters.
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