Novel Hydroperoxydioxolanes and ‐dioxanes by Hydroperoxide Rearrangement and Ozonolysis
Novel Hydroperoxydioxolanes and ‐dioxanes by Hydroperoxide Rearrangement and Ozonolysis
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DOI：
10.1002/ejoc.200500803
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发表时间：
2006-05
影响因子：
2.8
通讯作者：
H. Hamann;André Wlosnewski;T. Greco;J. Liebscher
中科院分区：
文献类型：
--
作者：
H. Hamann;André Wlosnewski;T. Greco;J. Liebscher
1-Indanols and 1-tetralols 8 with alkenyl substituents in the 1-position have been converted into the corresponding 1-hydroperoxides 9 by substitution under neutral conditions. Ozonolysis of the products gave rise to the formation of spiro-1,2-dioxolane and spiro-1,2-dioxane hydroperoxides 12. Alternative treatment of these 1-indanols and 1-tetralols 8 with hydrogen peroxide under acidic conditions caused substitution and hydroperoxide rearrangement to yield chroman-2-yl hydroperoxides 16 or open-chain unsaturated geminal bis-hydroperoxides 21. Ozonolysis of these products resulted in the formation of novel spiro-chromanes 18 and 20 with two oxygen atoms in the second ring or 3,5-bis(hydroperoxy)-1,2-dioxolanes or 3,6-bis(hydroperoxy)-1,2-dioxanes 23, respectively. All the products showed feeble antimalaria activity against chloroquine-resistant plasmodium falciparum. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
