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Issue 3, 2016
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Facile solvolysis of a surprisingly twisted tertiary amide

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Abstract

A bicyclo[2.2.2]octane derivative containing both a tertiary amide and a methyl ester (1) was shown crystallographically to adopt a conformation in which the amide is in the cis configuration, which is sterically disfavored, but electronically favored. The steric strain induces a significant torsion (15.9°) of the amide, thereby greatly increasing the solvolytic lability of the amide to the extent that we see competitive amide solvolysis in the presence of the normally more labile methyl ester also present in the molecule.

Graphical abstract: Facile solvolysis of a surprisingly twisted tertiary amide

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Publication details

The article was received on 12 Sep 2015, accepted on 03 Jan 2016 and first published on 05 Jan 2016


Article type: Paper
DOI: 10.1039/C5NJ02449H
Citation: New J. Chem., 2016,40, 1974-1981
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    Facile solvolysis of a surprisingly twisted tertiary amide

    A. J. Bloomfield, S. Chaudhuri, B. Q. Mercado, V. S. Batista and R. H. Crabtree, New J. Chem., 2016, 40, 1974
    DOI: 10.1039/C5NJ02449H

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