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

Synthesis and photochemical degradation of copper(II) ortho-azidobenzoate

“…Previously in the photolysis of ortho-azidobenzoic acid and potassium ortho-azidobenzoate [4], we found that the products of both singlet and triplet nitrene reactions were formed depending on the nature of the solvent. A special feature of the photolysis of the aqua complex consists in the photodegradation of the complex during which the azide group is coordinated to the copper(II) ion to form the chelate.…”

“…The TLC of the photolysis products of the aqua complex demonstrated that, at low radiation doses (irradiation time of 15-60 s), only two reaction products were formed: a light green spot due to copper(II) anthranilate with R f = 0 and a violet spot due to the chelate complex with R f = 0.47. The areas of these spots increased with radiation dose, and the spot area of the chelate complex was much greater than the spot area of copper(II) anthranilate; that is, the process of photodehydration occurs much more rapidly than the degradation of the azido group with the formation of the amino group [3,4]. A comparison between the absorption curves of copper(II) anthranilate (Fig.…”

“…The photochemical properties of aromatic azides depend on the nature of the organic radical (the positions and properties of substituents on the aromatic ring), as well as on the nature of surrounding molecules (solvent and various additives in solution and the relative arrangement of molecules in a crystalline, amorphous, or adsorbed state) [1][2][3][4]. Moreover, the azido group, which has lone electron pairs on nitrogen atoms [5], as well as other nitrogen-containing groups (amino, azo, and nitrilo) [6][7][8][9][10], can form coordination compounds with transition metals.…”

“…Fluorescence and spot test reactions for conceivably formed functional groups [4] were used for visualization. A chloroform-methanol solvent blend in a volume ratio of 4 : 1 was used as an eluant.…”

Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N–O bond-forming cyclization of 2-azidobenzoic acids

“…The structure of benzisoxazole 2a was determined by IR, 1 H and 13 C NMR spectroscopy and by comparison of its mass spectrum with the corresponding spectrum from the NIST library (NIST: 37717). In addition, the structure was confirmed by the alternative synthesis of 2a through the heterocyclization of 2-nitrobenzoic acid [ 28 – 29 ] and X-ray structure analysis [ 33 ].…”