Ritter Reaction Induced by Clay-Supported Ferric Nitrate

✍ Scribed by Eugenio Polla

• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 122 KB
• Volume: 94
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19850940113

✦ Synopsis

The Ritter reaction prepares amides by N-nucleophilic addition of a nitrile to a carbenium ion produced from an olefin or alcohol in presence of sulfuric acid and subsequent decomposition by vater of the quarternary ion formed. It currently enjoy8 a revival' : the reaction has been performed with alkyl halides3 and hydrocarbons4, using nitrosonium 1 salts. Clav-sumorted ferric nitrate ("clayfen") can be used as a nitrosating reagent5. This -..

prompted us to investigate the conversion of alkyl bromides to the corresponding amides.

Indeed the 5-alkyl bromides vere converted into the corresponding amides using this inexpensive "clayfen" reagent. according to:

1)=1670(s); V (amid0 II)=1540(8). 1b=%nr (CDC13, TMS ,ppm) 6 r ! 5 0 (S, 9H) ; 5.96( bs , 1H) ; 7.40-7.53(m, 3H ; 7.74(d,ZH,J=E.OHz); ir(nujo1 mull, cm-') : VNH=3280(m) ,3200(sh); V ~3030,3060(w); v (amide I)=1640 ( 8 ) ; vAr(CpC)=1600 ( w ) ; v ?amid0 I1 )=15SO(s~:o