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Communication | Regular issue | Vol 19, No. 12, 1982, pp.2275-2278
Published online, 1st January, 1970
DOI: 10.3987/R-1982-12-2275
Photochemical Ring Opening Rreactions of 3-Alkoxyisocoumarin and 3-Halo-1-isoquinolone

Chikara Kaneko, Toshihiko Naito, and Chiemi Miwa

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Irradiation of 3-methoxyisocoumarin (1) in an alcohol afforded two kinds of diester of homophthalic acid (3 and 4) and the mechanism including novel 1,5-sigmatropic methoxy rearrangement from initially formed ketene (5) to the isomeric ketene (6) was proposed. Similar photochemical ring opening reaction of 3-chloro- and -bromo-1-isoquinolones (8 and 9) as well as their novel photoalkoxylation reaction is also described.