Facile solvolysis of a surprisingly twisted tertiary amide

DOI

10.1039/c5nj02449h

Authors

Aaron J. Bloomfield, Yale University
Subhajyoti Chaudhuri, Yale University
Brandon Q. Mercado, Yale University
Victor S. Batista, Yale University
Robert H. Crabtree, Yale University

Peer Reviewed

1

Document Type

Journal Article

Publication Date

1-1-2016

Publication Title

New Journal of Chemistry

School

Bayer School of Natural and Environmental Sciences

Abstract

© The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016. 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.

Rights

© The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016.

Repository Citation

Bloomfield, A., Chaudhuri, S., Mercado, B., Batista, V., & Crabtree, R. (2016). Facile solvolysis of a surprisingly twisted tertiary amide. New Journal of Chemistry. https://doi.org/10.1039/c5nj02449h