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Synthesis and NMR spectra of 17oxygen enriched phenols

✍ Scribed by Shelton Bank; Kathryn L. Longley

Publisher: John Wiley and Sons
Year: 1990
Tongue: French
Weight: 428 KB
Volume: 28
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580280106

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✦ Synopsis

Abstract

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.

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