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Periodic Acid, a Novel Oxidant of Polycyclic, Aromatic Hydrocarbons *

Authors
  • Fatiadi, Alexander J.
Type
Published Article
Journal
Journal of Research of the National Bureau of Standards. Section A, Physics and Chemistry
Publisher
National Institute of Standards and Technology
Publication Date
Jan 01, 1968
Volume
72A
Issue
4
Pages
341–350
Identifiers
DOI: 10.6028/jres.072A.030
PMID: 31824100
PMCID: PMC6640608
Source
PubMed Central
Keywords
License
Unknown

Abstract

Certain polycyclic, aromatic hydrocarbons can be oxidized with periodic acid in aprotic solvents containing a small proportion of water. A unique, two-fold character of response to periodic acid by these hydrocarbons has been found: (1) production of a coupling reaction through a radical intermediate [conversion of pyrene into 1,1′-bipyrene, and fluorene into 1,2-bis(2,2′-biphenylylene)ethylene] or (2) conversion into quinones by a two-equivalent oxidation mechanism that does not involve a radical intermediate [acenaphthene, anthracene, anthrone, benz[ a ]anthracene, naphthacene, naphthalene, and phenanthrene]. Little or no reaction was observed when oxidation was attempted with sodium metaperiodate instead of periodic acid. Electron-spin resonance revealed no radical intermediate in the oxidation of malonic acid with either periodic acid or sodium periodate.

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