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

ABSTRACT: 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.

SUBMITTER: Restorp P

PROVIDER: S-EPMC2642476 | biostudies-literature | 2008 Sep

REPOSITORIES: biostudies-literature

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

Restorp Per P Rebek Julius J

Journal of the American Chemical Society 20080813 36

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. ...[more]

PMID: 18698780

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