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Synthesis of 2,1-benzisoxazol-3(1H)-one by intramolecular photochemical cyclization of 2-azidobenzoic acid.
Published:
31 October 2011
by MDPI
in The 15th International Electronic Conference on Synthetic Organic Chemistry
session General Organic Synthesis
Abstract: Peculiarities of 2,1-benzisoxazol-3(1H)-one synthesis by means of the photochemical cycle forming reaction of 2-azidobezoic acid in ethanol. Based upon HPLC kinetical data we have observed the 2,1-benzisoxazol-3(1H)-one yield decrease in the course of decreasing of the starting azide concentration. It was stated that the 2,1-benzisoxazol-3(1H)-one formation effectiveness depended on the actinic light wavelength. Changing the light wavelength from 365 to 253.7 nm we observed an increase of the cycle formation yield. The decrease of the 2,1-benzisoxazol-3(1H)-one yield in the course of irradiating at 365 nm was explained by the secondary photolysis.
Keywords: aromatic azide photochemistry, photochemical cyclization, 2,1-benzisoxazol-3(1H)-one, 2-azidobezoic acid, photolysis, nitrenes
