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Photolysis of ortho-Azidobenzoic Acid in Aqueous Solutions and Water–Organic Solvent Mixtures

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Abstract

The photolysis of o-azidobenzoic acid and its potassium salt in water, ethanol, tetrahydrofuran (THF), and ethanol–water and THF–water mixtures was studied by IR and UV spectroscopy and thin-layer chromatography. It was found that the photolysis of o-azidobenzoic acid and potassium o-azidobenzoate in aqueous solutions mainly resulted in 2,1-benzisoxazolone, the intramolecular cyclization product. The process of azepine formation in ethanol or an ethanol–water mixture depends on the nucleophilic nature of ethanol; in this case, water is practically of no importance. The presence of THF in an aqueous solution shifted the singlet nitrene–dehydroazepine equilibrium toward dehydroazepine, which reacts with water to give azepines.

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Authors and Affiliations

  1. Nizhni Novgorod State University, pr. Gagarina 23, Nizhni Novgorod, 603950, Russia

    A. V. Budruev, L. N. Karyakina & A. V. Oleinik

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  1. A. V. Budruev
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  2. L. N. Karyakina
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  3. A. V. Oleinik
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Budruev, A.V., Karyakina, L.N. & Oleinik, A.V. Photolysis of ortho-Azidobenzoic Acid in Aqueous Solutions and Water–Organic Solvent Mixtures. High Energy Chemistry 38, 20–24 (2004). https://doi.org/10.1023/B:HIEC.0000012059.38366.8e

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  • DOI: https://doi.org/10.1023/B:HIEC.0000012059.38366.8e

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