SYNTHESIS OF 2,1-BENZISOXAZOL-3(1H)-ONE BY INTRAMOLECULAR PHOTOCHEMICAL CYCLIZATION OF 2-AZIDOBENZOIC ACID |
| 4 | |
| 2012 |
| scientific article | 541.141.5; 544.526.1; 547.786.31; 547.236 | ||
| 129-134 | aromatic azide photochemistry, photochemical cyclization, 2,1-benzisoxazol-3(1H)-one, 2- azidobenzoic acid, photolysis, nitrenes |
| A photochemical cyclization reaction of 2-azidobenzoic acid in ethanol yielding 2,1-benzisoxazol-3(1H)-one is
studied by high-pressure liquid chromatography (HPLC). Based on HPLC kinetic data, we have established that an
increase of the azide concentration in the solution does not change the 2,1-benzisoxazol-3(1H)-one yield. This testifies
to its single route formation and an insignificant contribution of bimolecular processes to the cyclization reaction.
Average compound yields also suggest its nitrene rather than concerted mechanism of formation. Secondary
photolysis of 2,1-benzisoxazol-3(1H)-one may accompany its photochemical formation which leads to the decrease
in the main product yield. |
 |