Difluoromethyltrialkylammonium salts--their expeditious synthesis from chlorodifluoromethane and tertiary amines in the presence of concentrated aqueous sodium hydroxide. The catalytic process.
We found that difluorocarbene generated from chlorodifluoromethane with 50% aqueous sodium hydroxide reacts with lipophilic tertiary amines 1a-g giving difluoromethyltrialkylammonium chlorides 2a-g in high yields. Similarly, difluoromethyltrialkylammonium iodides 3h-l, nitrates 4h-k, or isothiocyanates 5i,j were synthesized from hydrophilic tertiary amines 1h-l and the corresponding sodium or potassium salts. The process is catalytic with respect to the base used.
Faculty of Chemistry, Warsaw University of Technology, Koszykowa 75, 00-662 Warsaw, Poland.
Ewelina
E
Nawrot
Andrzej
A
Joñczyk
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D005617:Chlorofluorocarbons, Methane / Q000737:chemistry*; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012492:Salts / Q000138:chemical synthesis / Q000737:chemistry; D012972:Sodium Hydroxide / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D000588:Amines; D005617:Chlorofluorocarbons, Methane; D000644:Quaternary Ammonium Compounds; D012492:Salts; D014867:Water; D012972:Sodium Hydroxide; C009755:fluorocarbon 22