Mechanism of Methyl Esterification of Carboxylic Acids by Trimethylsilyldiazomethane | Zendy

Kühnel Erik | Zendy; Laffan David D. P. | Zendy; LloydJones Guy C. | Zendy; Martínez del Campo Teresa | Zendy; Shepperson Ian R. | Zendy; Slaughter Jennifer L. | Zendy

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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).

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