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. 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

Per Restorp  1 , Julius Rebek Jr
Affiliations

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

Per Restorp et al. J Am Chem Soc. .

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.

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Figures

Figure 1
Figure 1
1H NMR spectra of cavitand 1 and iPrNC. Blue square shows intermediate A and red circle product B.
Figure 2
Figure 2
IR spectra of cavitand 1 and iPrNC.
Scheme 1
Scheme 1
Reaction of cavitand 1 with aliphatic isonitriles.
See this image and copyright information in PMC

References

    1. Cram DJ. Science. 1983;219:1177–1183. - PubMed
    2. Rudkevich DM, Rebek J., Jr Eur. J. Org. Chem. 1999:1991–2005.
    3. Purse BW, Rebek J., Jr Proc. Natl. Acad. Sci. U.S.A. 2005;102:10777–10782. - PMC - PubMed
    1. Kemp DS, Petrakis KS. J. Org. Chem. 1981;46:5140–5143.
    1. Wash PL, Renslo AR, Rebek J. Angew. Chem. Int. Ed. Engl. 2000;40:1221–1222. - PubMed
    2. Iwasawa T, Wash PL, Gibson C, Rebek J. Tetrahedron. 2007;63:6506–6511. - PMC - PubMed
    3. Renslo AR, Rebek J. Angew. Chem. Int. Ed. 2000;40:3281–3283. - PubMed
    4. Purse BW, Rebek J. Proc. Natl. Acad. Sci., U.S.A. 2006;103:2530–2534. - PMC - PubMed
    1. Butterfield SM, Rebek J. J. Am. Chem. Soc. 2006;128:15366–15367. - PubMed
    1. Iwasawa T, Hooley RJ, Rebek J., Jr Science. 2007;317:493–496. - PubMed
    2. Hooley RJ, Restorp P, Iwasawa T, Rebek J., Jr J. Am. Chem. Soc. 2007;129:15639–15643. - PubMed

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