Synthesis ofE,E-diene hydroperoxides via photoisomerization of protected hydroperoxides |
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| Authors: | P. H. Dussault I. Q. Lee C. T. Eary |
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| Affiliation: | (1) Department of Chemistry, University of Nebraska-Lincoln, 68588-0304 Lincoln, Nebraska |
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| Abstract: | A general approach toE,E-diene hydroperoxides is described based upon photoisomerization of readily availableZ,E-diene monoperoxyketals. Protection of aZ,E-diene hydroperoxide as the 2-methoxypropyl peroxyketal is followed by iodine-mediated photoisomerization to produce a mixture enriched in theE,E isomer. After chromatographic purification, deprotection of the peroxyketal with mild acid furnishes theE,E-diene hydroperoxide. |
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