Potter, GT, Jayson, GC, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 and Gardiner, JM (2015) Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids. Tetrahedron Letters, 56 (37). 5153 - 5156.

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Abstract

A series of aromatic and heteroaromatic primary amides were converted directly to carboxylic acids by heating with amyl nitrite in acetic acid. Most conversions proceeded to give reasonable to excellent yields on a range of substrates containing various functional groups. This reagent system is thus applicable for the direct hydrolysis of a range of different primary carboxamides. The reaction with a phenolic aromatic substrate afforded two alternative nitration products as major outcomes, evidencing alternative reaction pathways resulting from the free phenolic OH.

Item Type: Article
Uncontrolled Keywords: Primary amide, Carboxylic acid, Nitration, Diazotization
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Natural Sciences > School of Physical and Geographical Sciences
Related URLs:
Depositing User: Symplectic
Date Deposited: 26 Nov 2015 11:08
Last Modified: 24 Apr 2019 08:50
URI: http://eprints.keele.ac.uk/id/eprint/1218

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