Name: 1,2-Benzisoxazole. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 1,2-Benzisoxazole, is researched, Molecular C7H5NO, CAS is 271-95-4, about Photoisomerization of 4-hydroxybenzonitrile into 4-hydroxybenzoisonitrile.
In deoxygenated water, methanol, and ethanol, 4-hydroxybenzonitrile (4-HBN) is photoisomerized into 4-hydroxybenzoisonitrile (4-HBIN; 4-isocyanatophenol), which is then hydrolyzed into 4-hydroxyformanilide in acidic medium. In slightly acidic (pH 5.4) or moderately alk. (pH 9.4) solutions as well as in alcs., the reaction proceeds with a chem. yield exceeding 85%. The triplet-triplet absorption of 4-HBN (λmax=300 nm) is detected by transient absorption spectroscopy; the intersystem crossing quantum yields are Fisc=0.14 in neutral water and Fisc=0.45 in ethanol. The triplet is converted into long-lived transients absorbing in the far UV. The cyanophenolate ion (λmax=275 nm) is transiently produced upon excitation of moderately acidic solutions, with a quantum yield of 0.082; this process is possible because of the high acidity of the excited singlet. The anal. of the kinetics of 4-HBIN formation as a function of irradiating photon flux shows that the photoisomerization of 4-HBN is a two-stage photoprocess. According to triplet-quenching studies, the first stage proceeds via the 4-HBN triplet to yield an intermediate capable of absorbing a second UV photon, which then gives 4-HBIN in the second stage. Mechanistic considerations indicate that this intermediate is likely to be an azirine.
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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI