Synthesis of nine-, ten-, and fifteen-membered alkenolides by the oxidative cleavage of the bridging C=C bond in 2-oxabicycloalkenes |
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Authors: | Ogibin,Yu. N.,Terent" ev,A. O.,Ananikov,V. P.,Nikishin,G. I. |
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Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | Hydroperoxidation of C=C-bridged 2-oxabicycloalkenes in which the five- or six-membered oxacycle is fused with the five-, six-, or twelve-membered hydrocarbon ring was studied. The Cu(OAc)2-catalyzed decomposition of the resulting hydroperoxides afforded nine-, ten-, or fifteen-membered trans-alkenolides, respectively. The latter compounds were obtained as pairs of regioisomers, with the isomers in which the double bond is more remote from the ether oxygen atom predominating. |
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Keywords: | synthesis nine-, ten- and fifteen-membered alkenolides 2-oxabicycloalkenes hydroperoxidation hydrogen peroxide 1-hydroperoxy-2-oxabicycloalkanes catalytic decomposition of hydroperoxides copper diacetate |
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