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Synthesis, 1 H‐NMR and mass spectra of 2‐ 2 H‐, 2,3‐ 2 H 2 ‐ and 2,2‐ 2 H 2 ‐labelled short chain carboxylic acids
Author(s) -
Hine David G.,
Ikeda Yasuyuki,
Tanaka Kay
Publication year - 1985
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580220406
Subject(s) - chemistry , mass spectrum , nmr spectra database , spectral line , mass spectrometry , physics , chromatography , astronomy
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.