Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.
A deep cavitand with an inwardly directed carboxylic acid function reacts with small aliphatic isonitriles to form N-acyl formamides inside the cavity. The unique isolation and stabilization of covalently bound guests within the structured environment of the cavitand allows for observation of the labile O-acyl isoimide intermediate using conventional spectroscopic methods.
Restorp
Per
P
The Skaggs Institute for Chemical Biology, 10550 North Torrey Pines Road, La Jolla, California, 92037, USA.
Rebek
Julius
J
D002264:Carboxylic Acids / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D005559:Formamides / Q000138:chemical synthesis / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D009570:Nitriles / Q000737:chemistry*; D012118:Resorcinols / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
D002264:Carboxylic Acids; D004988:Ethers, Cyclic; D005559:Formamides; D007094:Imides; D009570:Nitriles; D012118:Resorcinols; C442939:cavitand