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Mechanism of Methyl Esterification of Carboxylic Acids by Trimethylsilyldiazomethane
Author(s) -
Kühnel Erik,
Laffan David D. P.,
LloydJones Guy C.,
Martínez del Campo Teresa,
Shepperson Ian R.,
Slaughter Jennifer L.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200702131
Subject(s) - diazomethane , chemistry , carboxylic acid , deuterium , organic chemistry , mechanism (biology) , catalysis , philosophy , physics , epistemology , quantum mechanics
Minimal hazard : A deuterium‐labeling study reveals that, contrary to prior assumption, the safe, reliable, and widely adopted method for methyl esterification of carboxylic acids using trimethylsilyldiazomethane (TMSCHN 2 ) proceeds through the concurrent acid‐catalyzed methanolytic liberation of diazomethane (see scheme).