On the Synthesis of N-Sulfonyl Substituted Imidoyl Azides

✍ Scribed by Gerrit L'abbé; Alex van Asch; Françoise Godts

• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 93 KB
• Volume: 92
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19830920112

✦ Synopsis

The high reactivity of imidoyl chlorides in nucleophilic displacement reactions is related to their facile isomerization into nitrilium ions.' with the azide ion to give imidoyl azides which may equilibrate with tetrazoles depending on the nature of the substituents, temperature and solvent used. For instance, & and 2 exist in the open-chain azide form2 whereas N-alkyl and Naryl substituted imidoyl azides occur mostly in the tetrazole form 2.