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Face Selectivity in the Reduction with Dideuteriodi-imide of Endoperoxides derived from the Singlet Oxygenation of Cycloalka-1,3-dienes

DOI: 10.1039/P29840002069

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 2069 - 2072 (1984)

Update date:2022-08-10

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Authors:

Bloodworth, A. J.Bloodworth, A. J.

Eggelte, Henny J.Eggelte, Henny J.

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Article abstract of DOI:10.1039/P29840002069

Four dioxabicycloalkenes (n = 1-4) have been reduced with dideuteriodi-imide.For each reduction, the ratio of the amount of product arising from cis-addition of two deuterium atoms to the face of the double bond syn to the dioxygen bridge to that arising from addition to the anti face has been determined by 1H-decoupled 2H n.m.r. spectroscopy, and the structures of the individual isomers have been determined by 1H n.m.r. spectroscopy.The cyclopentadiene endoperoxide (n = 1) yields exclusively the anti-isomer, whereas the cyclohexadiene endoperoxide (n = 2) affords a mixture containing 66percent of syn isomer, and the cycloheptadiene and cyclo-octadiene endoperoxides (n = 3 and 4) give only the syn isomer.The results are consistent with the expected variation across the series in both electronic and steric effects.

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Product name:2,3-Dioxabicyclo[2.2.1]heptane

Cas No:279-35-6

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