Abstract
On catalytic hydrogenation over Pd-C under normal conditions cubane (10) takes up 3 mol of hydrogen in a few hours. Bicyclo[2.2.2] octane (13) is formed as the main product, and tetracyclo[4.2.0.02,5.03,8]octane (11, secocubane) and tricyclo[4.2.0.02,5]octane (12,nortwistbrendane) have been identified as intermediates. The hydrogenolysis of dimethyl 1,4-cubane dicarboxylate, as well as cuneane derivatives, have also been studied. Results are discussed in terms of strain relief calculated by the molecular mechanics method for cubane-like structures.
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