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Synthesis, 1H-NMR and mass spectra of 2-2H-, 2,3-2H2- and 2,2-2H2-labelled short chain carboxylic acids

✍ Scribed by David G. Hine; Yasuyuki Ikeda; Kay Tanaka


Publisher
John Wiley and Sons
Year
1985
Tongue
French
Weight
437 KB
Volume
22
Category
Article
ISSN
0022-2135

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✦ Synopsis


Abstract

2‐^2^H, 2,3‐^2^H~2~ and 2,2‐^2^H~2~ ‐ short chain carboxylic acids were synthesized. Monodeuteration at the 2‐position of the carboxylic acids was achieved via decarboxylation of the corresponding carboxyldeuterated 2‐alkylmalonic acids. 2,3‐Dideuteration was achieved via catalytic deuteration of the corresponding 2,3‐ unsaturated carboxylic acids with sodium borodeuteride. 2,2‐Dideuteration was achieved via repeated base catalyzed exchange reactions of the carboxylate sodium salts in sodium deuteroxide/deuterium oxide solution. Proton nuclear magnetic resonance and mass spectra of the obtained products are presented.


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