Synthèse de nouvelles propenanidines n-substituées a partir de sels de nitrilium[1]

✍ Scribed by Marc Van Den Bril; Robert Fuks

• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 268 KB
• Volume: 89
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19800890605

✦ Synopsis

Abstract

A number of N‐t‐butylpropenamidines V have beer, prepared for the first time by amination of N‐t‐butylacrylonitrilium [IIIb] or N‐t‐butylmethacrylonitrilium tetrachloroferrate (IIIc). The salts IIIb and IIIc are easely prepared at −40°C within a few minutes from the corresponding nitrile, t‐butyl chloride and ferric chloride. The amination [with primary or secondary aliphatic or aromatic amines] should be started at −70 °C to ensure a smooth reaction and to give high yields of amidine V, because the nitrilium salts are unstable above −10 °C. This method represents an easy one‐pot synthesis of N‐t‐butyl substituted propenamidines from the corresponding nitrile I.