The stereochemistry of the palladium-catalysed hydrogenation of allenes

The Heterogeneous Catalytic Hydrogenation of Cumulated Allene-cyclopropanes: 1-(2′-Methylpropenylidene)-7-bicyclo[4.1.0]heptane

“…The catalytic hydrogenation of allenes is particularly responsive to the `catalyst hindrance' presented by dierent orientations of the allene to the hydrogen adsorbed on the catalyst surface. 3,4 Indeed such hindrance eects can provide a means of converting molecular dissymmetry into centrodissymmetry, hence allowing an experimental determination of the absolute con®guration of an optically active allene. 5 The hydrogenation of 1-(2-methylpropenylidene)-7-bicyclo-[4.1.0]heptane 1 over Pt was followed using GLC `snapshot analysis' (Graph 1).…”