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Synthesis and NMR spectra of 17 oxygen enriched phenols
Author(s) -
Bank Shelton,
Longley Kathryn L.
Publication year - 1990
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.2580280106
Subject(s) - chemistry , phenols , phenol , autoxidation , oxygen , potassium , nmr spectra database , aryl , oxygen atom , organic chemistry , medicinal chemistry , nuclear chemistry , spectral line , molecule , physics , alkyl , astronomy
An efficient and convenient method of preparing 17 O enriched phenols is described. Aryl boronic acids are oxidized with 17 O enriched potassium hydroperoxide. The 17 O labeled potassium hydroperoxide is prepared from the autoxidation reaction of benzhydrol with 17 O enriched oxygen gas in the presence of potassium t‐butoxide. [0–17]Phenol, p‐bromo[0–17]phenol and p‐methoxy[0–17]phenol were prepared in good to modest overall chemical yields (40–60%) and high isotopic retention (82–90% from 16.8 atom % 17 O 2 starting material). 17 O NMR spectra of the three enriched phenols demonstrate the benefits of using enriched samples in reducing the total experiment time and greatly improving the signal‐to‐noise ratio compared to unenriched samples.