EventsThe 15th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-15-00584
This submission belongs to the session a. General Organic Synthesis of the event The 15th International Electronic Conference on Synthetic Organic Chemistry
Published date
31 Oct, 2011
Citation
Olga A Kuzmicheva, Darja Y Sinjagina, Andrei V Budruev, Synthesis of 2,1-benzisoxazol-3(1H)-one by intramolecular photochemical cyclization of 2-azidobenzoic acid., in Proceedings of The 15th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2011, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-15-00584
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Synthesis of 2,1-benzisoxazol-3(1H)-one by intramolecular photochemical cyclization of 2-azidobenzoic acid.

Olga A Kuzmicheva 1
Darja Y Sinjagina 1
Andrei V Budruev 1
1. Nizhnii Novgorod State University, Gagarin Ave., 23, Nizhnii Novgorod, 603950, Russia.
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
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