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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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Article information


Submitted
12 Sep 2015
Accepted
03 Jan 2016
First published
05 Jan 2016

This article is Open Access

New J. Chem., 2016,40, 1974-1981
Article type
Paper
Author version available

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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