A Novel Direct Conversion of Primary Amides to Their Corresponding Methyl Esters

A novel method was used to directly convert aliphatic and aromatic primary amides into their corresponding methyl esters in high yields (up to 99 %) under mild reaction conditions. Possible mechanisms were studied at the B3LYP/6‐31++G(d,p) level of theory. Formation of the ester proceeded through a...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2007-02, Vol.2007 (6), p.1026-1030
Main Authors: Li, Liang-Chun, Ren, Jie, Liao, Tou-Gen, Jiang, Ju-Xing, Zhu, Hua-Jie
Format: Article
Language:English
Subjects:
Amides
Density functional calculations
Esters
Reaction Mechanisms
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Summary:A novel method was used to directly convert aliphatic and aromatic primary amides into their corresponding methyl esters in high yields (up to 99 %) under mild reaction conditions. Possible mechanisms were studied at the B3LYP/6‐31++G(d,p) level of theory. Formation of the ester proceeded through a rearrangement of the –OMe and –NH2 groups in the RC(O)NHS(O)OMe intermediate in a H+‐catalyzed six‐membered ring transition state structure. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200600853