Tetrahedron p. 1757 - 1762 (1986)
Update date:2022-07-29
Topics:
Stober, Reinhard
Musso, Hans
Osawa, Eiji
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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Doi:10.1021/jo00012a021
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