Photolysis of p-Toluenesulfonyl Azide and Its Charge-Transfer Complex with Aniline

Article abstract of DOI:10.1021/jo00160a024

Photolysis of p-toluenesulfonyl azide (1) in p-xylene and cyclohexane gives primarily the products derived from insertion of (p-tolylsulfonyl)nitrene into the solvent.For p-xylene, an unstable intermediate product is formed which decomposes in the dark at room temperature to give both the ring-insertion product and the corresponding p-toluenesulfonamide (2).Photolysis of the ground-state charge-transfer complex between p-toluenesulfonyl azide and aniline gives six products, the major product being the sulfonyl hydrazide 7.Furthermore, formation of the insertion product by reaction with the solvent provides evidence for production of (p-tolylsulfonyl)nitrene from the excited charge-transfer complex.