Decomposition of aromatic azides in ethanethiol

✍ Scribed by Susan E. Carroll; Barry Nay; Eric F.V. Scriven; Hans Suschitzky; Desmond R. Thomas

• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 150 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)83190-7

✦ Synopsis

Photolytic decomposition of phenyl azide in ethanethiol gives o-thioethoxyaniline (1) in 39% yield. This is an unexpected result as phenyl azide usually undergoes ring expansion to 2-substituted 3H-azepines when decomposed in nucleophilic solvents, such as primaryl, secondary', and tertiary2 3 aliphatic amines, methanol , and hydrogen sulphidediethyl ether4. Photolysis of I-asidoquinoline and 8-azidonaphthalene in ethanethiol gives 8-thioethoxy-7-aminoquinoline (2) (48%) and 2-thioethoxy-1-naphthylamine (3) (40X;), which is comparable to their conversion into o-diamines on photolysis in secondary amines 5 . The