Electron spin resonance studies of photo-oxidation by metal ions in rigid media at low temperatures. Part 1.—Ce(IV) photo-oxidation of alcohols
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Transactions of the Faraday Society
- Vol. 67, 56-66
- https://doi.org/10.1039/tf9716700056
Abstract
Photolysis of deoxygenated solutions of ceric perchlorate and ceric ammonium nitrate in alcoholic, aqueous alcoholic and water + alcohol + acetonitrile solutions at 77 K by light of wavelength >300 nm leads to formation of radicals derived from the alcohol identified by electron spin resonance (e.s.r.) spectroscopy. Primary alcohols RCH2OH yield RĊHOH but secondary alcohols R2CHOH yield R· in addition to, and sometimes to the exclusion of R2ĊOH. Tertiary alcohols always give an alkyl fragment, e.g. C2H5· from tert-amyl alcohol. Allylic alcohols produce the corresponding hydroxyallyl radical and 1,2-diphenylethanol gives a spectrum of benzyl radical, indicating C—C cleavage. The mode of photo-oxidation by Ce(IV) clearly parallels that of the corresponding thermal oxidation.Keywords
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