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A two‐step synthesis of deuterium labeled 8, 8, 9, 9‐ d 4 ‐hexadecane from nonanoic acid
Author(s) -
Zhou Lei,
Bian Xinyu,
Yang Shizhong,
Mu Bozhong
Publication year - 2012
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.1962
Subject(s) - chemistry , deuterium , hexadecane , hydrogen–deuterium exchange , alkane , mass spectrometry , hydrogen , organic chemistry , chromatography , hydrocarbon , physics , quantum mechanics
Labeled compounds are essential in elucidating metabolic mechanisms and reaction pathways. A two‐step synthesis of deuterium‐labeled 8, 8, 9, 9‐ d 4 ‐hexadecane from nonanoic acid is described here. The synthesis procedures involved hydrogen–deuterium exchange of nonanoic acid with 3.00 m DCl‐D 2 O and then Kolbe electrolysis of the deuterated nonanoic acid to achieve the desired n ‐alkane that was confirmed by gas chromatography‐mass spectrometry and 1 H nuclear magnetic resonance. This method might provide an alternative route for the preparation of specifically deuterated alkanes of different chain lengths (C > 4) in which deuterium atoms are located at two adjacent carbons of the alkane's carbon chain. Copyright © 2012 John Wiley & Sons, Ltd.