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Issue 23, 2008
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Synthesis of 1-hydroperoxy-1′-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers

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Abstract

It was found that iodine-catalyzed reactions of geminal bishydroperoxides with acetals proceed with the replacement of only one alkoxy group by the peroxide group to give previously unknown structures of 1-hydroperoxy-1′-alkoxyperoxides in yields up to 64%. The same compounds are formed in the iodine-catalyzed reactions of geminal bishydroperoxides with enol ethers. The nature of the solvent has a decisive influence on the formation of 1-hydroperoxy-1′-alkoxyperoxides. In the series of Et2O, THF, EtOH, CHCl3, CH3CN, and hexane, the best results were obtained with the use of Et2O or THF as the solvent.

Graphical abstract: Synthesis of 1-hydroperoxy-1′-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers

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Publication details

The article was received on 09 Jun 2008, accepted on 01 Sep 2008 and first published on 20 Oct 2008


Article type: Paper
DOI: 10.1039/B809661A
Citation: Org. Biomol. Chem., 2008,6, 4435-4441
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    Synthesis of 1-hydroperoxy-1′-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers

    A. O. Terent'ev, M. M. Platonov, I. B. Krylov, V. V. Chernyshev and G. I. Nikishin, Org. Biomol. Chem., 2008, 6, 4435
    DOI: 10.1039/B809661A

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