Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis

Author(s)
Foley, Megan A.; Jamison, Timothy F.
Thumbnail
DownloadMAF TFJ OPRD 2010.pdf (391.4Kb)
PUBLISHER_POLICY
Terms of use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Metadata
Show full item record
Abstract
A rapid carboxylic acid-promoted lactone aminolysis is reported. A number of carboxylic acids were found to promote this amide bond-forming transformation, with aliphatic acids being the most efficient. This reaction is an equilibrium process (K[subscript eq] ≈ 1.8), and mechanistic investigations are consistent with mediation of a kinetically important proton-transfer step by the carboxylate, i.e., the conjugate base of the acid employed.
Date issued
2010-08
URI
http://hdl.handle.net/1721.1/76282
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Organic Process Research & Development
Publisher
American Chemical Society (ACS)
Citation
Foley, Megan A., and Timothy F. Jamison. “Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis.” Organic Process Research & Development 14.5 (2010): 1177–1181.
Version: Author's final manuscript
ISSN
1083-6160
1520-586X
Collections