1H NMR aided elucidation of products derived from photodegradation of ethyl 3-azido-4,6-difluorobenzoate in 2,2,2-trifluoroethanol

The major products formed upon photolysis of ethyl 3-azido-4,6-difluorobenzoate in 2,2,2,-tri-fluoroethanol-d(3) has been elucidated by H-1 NMR analysis of the product mixture. Among the products Formed and structurally elucidated was a hitherto unreported product formed during photolysis of aryl azides, namely azoxybenzene 19. The structural assignments of the major components of the reaction mixture were aided by comparison with H-1 NMR data from synthetic reference materials and compound isolation. MS, MS/MS, and HPLC analysis as well as UV spectroscopy was also employed in order to confirm and aid the structural analysis. (C) 2009 Elsevier Ltd. All rights reserved.