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• 6383-11-5 benzocyclobutene-1,2-dione 
• 938-24-9 indantrione 

Relevant academic research and scientific papers

Photochemistry of Benzocyclobutene-1,2-dione Studied by Laser Flash Photolysis with UV/VIS and IR Detection

Kinetic behaviour of bisketene generated by the photolysis of benzocyclobutene-1,2-dione in solution was investigated by TRIR and it was found that the formation of pyridine ylide could be explained by the reaction of pyridine with the bisketene, not oxacarbene.

Photolysis of indan-l,2-dione derivatives in oxygen-doped argon matrix at low temperature

Photolysis of indan-l,2,3-trion (la), benzo[ft]furan-2,3-dione (lb), 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.

First measurements of absolute rate constants for oxacarbene intermediates produced in the photochemistry of benzocyclobutenedione

The photochemistry of benzocyclobutenedione in solution has been examined by use of laser flash photolysis techniques. Two rapid processes appear to compete. One leads to the formation of the long-lived bisketene IV, which can be readily observed (λmax 380 nm). The other process leads to oxacarbene III. This carbene could not be monitored directly, but probing techniques, with pyridine and adamantanethione as probes, lead to readily detectable ylides that can be employed to characterize the kinetic behavior of III. Thus, III lives about 20 μs in toluene and can be trapped by typical carbene scavengers such as alcohols. Carbene trapping by alcohols is in fact a complex reaction, since it also leads to equilibration with a short-lived intermediate (studied in detail in methanol/acetonitrile) that in turn can be trapped by alcohols, azides, and halides. This intermediate is tentatively assigned to carbocation VIII formed by solvent protonation of III.