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J Am Chem Soc. 2008 Sep 10;130(36):11850-1. doi: 10.1021/ja803854r. Epub 2008 Aug 13.

Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.

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  • 1The Skaggs Institute for Chemical Biology, 10550 North Torrey Pines Road, La Jolla, California, 92037, USA.


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.

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