Facile solvolysis of a surprisingly twisted tertiary amide
Author:
Affiliation:
1. Department of Chemistry
2. Yale University
3. New Haven
4. USA
5. Energy Sciences Institute
6. West Haven
7. Yale School of Engineering and Applied Science
Abstract
A twisted 3° amide is cleaved at the same rate as a methyl ester under alkaline conditions at 22 °C.
Funder
National Science Foundation
Basic Energy Sciences
Publisher
Royal Society of Chemistry (RSC)
Subject
Materials Chemistry,General Chemistry,Catalysis
Link
http://pubs.rsc.org/en/content/articlepdf/2016/NJ/C5NJ02449H
Reference40 articles.
1. Studies on the Stability of Amides. I. Hydrolysis Mechanism of N-Substituted Aliphatic Amides
2. Amide bond formation and peptide coupling
3. Amide bond formation: beyond the myth of coupling reagents
4. Relationship between amidic distortion and ease of hydrolysis in base. If amidic resonance does not exist, then what accounts for the accelerated hydrolysis of distorted amides?
5. Distorted amides: correlation of their enhanced solvolysis with local charge depletions at the carbonyl carbon
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