Bicyclanes—II : On the preparation and halogenation of bicyclo[2,2,2]octane☆

Add time:08/19/2019    Source:sciencedirect.com

In the presence of traces of acidic materials, Diels-Alder condensation of ethylene and cyclohexadiene-1,3 gives, besides the expected bicyclo[2,2,2]octene-2, the isomeric bicyclo[3,2,1] octene-2; the latter is formed through acid-catalysed rearrangement. Its structure was proved among other things by stepwise oxidative degradation to cyclopentane-cis-1,3-dicarboxylic acid.Competitive halogenations of bicyclo[2,2,2]octane and cyclohexane showed that the methylene groups in the latter are somewhat more reactive. Reactivity ratios decreased at increasing temperatures.The reactivity of the bridgehead positions in bicyclo-octane towards hydrogen removal is appreciably larger than that of the methylene groups, in contrast to the situation in bicyclo[2,2,1]-heptane. This is probably due to the greater flexibility of the bicyclo-octane skeleton permitting a near-planar configuration at the bridgehead. Some of the differences between the bicyclo[2,2,2]octane, bicyclo[2,2,1]heptane and cyclohexane systems are briefly discussed.

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