Carbon–carbon bond scission during the reactions of allylic hydroperoxides with some transition metal compounds. Results relevant to a recent proposal
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 4,p. 381-383
- https://doi.org/10.1039/c39920000381
Abstract
The proposal that 4-exo closure of an allylic peroxyl radical can account for the titled reactions of pinocarveyl hydroperoxide has been considered in the light of literature data, along with the results of reactions carried out with a range of alternative copper and iron reagents and with the previously examined reagents in the presence or absence of suitable traps: an acid-catalysed pathway is proposed to account for the observed scission reaction.Keywords
This publication has 6 references indexed in Scilit:
- Catalysed oxygenation of allylic hydroperoxides derived from qinghao (artemisinic) acid. Conversion of qinghao acid into dehydroginghaosu (artemisitene) and qinghaosu (artemisinin)Journal of the Chemical Society, Chemical Communications, 1990
- Iron(III)-induced cleavage of cyclic allylic hydroperoxides to dicarbonyl compounds under aprotic conditionsJournal of the Chemical Society, Chemical Communications, 1990
- Iron(III) and copper(II) catalysed transformations of fatty acid hydroperoxides: efficient generation of peroxy radicals with copper(II) trifluoromethanesulphonateJournal of the Chemical Society, Chemical Communications, 1990
- Mechanisms of antioxidant action. Part 4. The decomposition of 1-methyl-1-phenylethyl hydroperoxide by zinc dialkyldithiocarbamates and zinc xanthatesJournal of the Chemical Society, Perkin Transactions 2, 1985
- Acid-catalyzed intramolecular "Diels-Alder" reactions. The cycloaddition of allyl cations to 1,3-dienesJournal of the American Chemical Society, 1984
- The allylic rearrangement of hydroperoxides: the allylperoxyl radicalJournal of the Chemical Society, Perkin Transactions 2, 1984