Direct evidence for base-mediated decomposition of alkyl hydroperoxides (ROOH) in the gas phase

Blanksby, Stephen J., Ellison, G. B., Bierbaum, V. M., & Kato, S. (2002) Direct evidence for base-mediated decomposition of alkyl hydroperoxides (ROOH) in the gas phase. Journal of the American Chemical Society, 124(13), pp. 3196-3197.

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Abstract

Alkyl hydroperoxides (ROOH) are attributed a key role in the biochemical oxidation of lipids during oxidative stress.1 In this chemistry ROOH compounds, where the R groups are unsaturated fatty acids, are viewed as transient ntermediates which are readily degraded, due to the lability of the RO-OH bond, to yield potentially genotoxic aldehydes and ketones.2 Generally, the decomposition of alkyl hydroperoxides is thought to be mediated by radical abstraction or electron transfer processes usually involving enzymes, transition metals, or recently, Vitamin C.3 In this paper we present the first unambiguous experimental and computational evidence for base-mediated heterolytic decomposition of simple alkyl hydroperoxides by the mechanism outlined in Scheme 1.

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ID Code: 71647
Item Type: Journal Article
Refereed: Yes
Additional URLs:
Keywords: chemistry, hydrogen
DOI: 10.1021/ja017658c
ISSN: 1520-5216 (online) 0002-7863 (print)
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Copyright Owner: Copyright © 2002 American Chemical Society
Deposited On: 21 May 2014 01:50
Last Modified: 21 May 2014 01:50

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