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Novel Hydroperoxydioxolanes and ‐dioxanes by Hydroperoxide Rearrangement and Ozonolysis
Author(s) -
Hamann HansJürgen,
Wlosnewski André,
Greco Tonino,
Liebscher Jürgen
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500803
Subject(s) - chemistry , ozonolysis , hydrogen peroxide , yield (engineering) , medicinal chemistry , geminal , peroxide , oxygen atom , oxygen , autoxidation , stereochemistry , organic chemistry , molecule , materials science , metallurgy
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)