Tetrahedron Letters p. 9747 - 9750 (1998)
Update date:2022-08-11
Topics:
Sakurai, Tadamitsu
Kubo, Kanji
Kojima, Shunsuke
Shoro, Takuya
Inoue, Hiroyasu
Irradiation of the title compound having a 9-anthryl (1a) or a 1- pyrenyl group (1b) in methanol was found to give the heterolytic C-O bond cleavage products: 1-hydroxy-2-pyridone and arylmethyl methyl ether, (which predominate for the reaction of 1a), along with 2-pyridone, aryl-substituted methanol and aryl aldehyde derived from the homolysis of the N-O bond (that mainly occurs in the photolysis of 1b). Spectroscopic analysis of the ground- state and excited singlet-state behavior of 1 revealed that a non-emissive intramolecular exciplex (whose formation rate is much faster in 1a than in 1b) plays a key role in inducing the C-O bond heterolysis.
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