Abstract
Abstract Photolysis of indan-1,2,3-trion (1a), benzo[b]furan-2,3-dione (1b), and N-methylisatin (1c) in argon matrix either with or without oxygen at 10 K was investigated by IR spectroscopy in combination with DFT calculations. The results indicate that while 1a and 1b gave the products mixture as a result of α-cleavage, followed by decarbonylation, 1c was rather photostable under similar conditions. However, when the irradiation was carried out in argon matrix doped with 20% oxygen, 1c decomposed much more efficiently than that in argon matrix and cyclic diacyl peroxide presumably formed by trapping of initial diradical originating from α-cleavage by molecular oxygen was detected. Similar irradiation of 1b also gave cyclic diacyl peroxide along with photodecarbonylation products, but irradiation of 1a in oxygen-doped matrix produced not only cyclic diacyl peroxide but also products as a result of oxidation of photodecarbonylation product. The present observation reveals that photolysis of ketones in oxygen-doped matrix at low temperature provides useful information concerning the reactivities of ketones toward α-cleavage.
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