Catalytic hydrogenation
6 real reactions from the literature, on six-membered cycloalkenes, furans, trisubstituted six-membered cycloalkenes and α,β-unsaturated ketones. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
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Hydrogenation: diethyl cyclohex-4-ene-1,2-dicarboxylate (a six-membered cycloalkene) with H2 (2 atm); Pt (or Pd/C) gives 1,2-diethyl 1,2-cyclohexanedicarboxylate (the saturated product).
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Hydrogenation: furan with H2 (100 psi); PdO gives tetrahydrofuran (the saturated product).
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Hydrogenation: a trisubstituted six-membered cycloalkene with H2 / PtO2; AcOH gives the saturated product.
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Hydrogenation: chalcone (an α,β-unsaturated ketone) with H2 (3 atm), PtO2; CH3CH2OAc gives dihydrochalcone (the saturated product).
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Hydrogenation: (1Z,5E,9E)-cyclododeca-1,5,9-triene (a 12-membered cycloalkene) with H2NNH2, air, CuSO4; CH3CH2OH, H2O gives cyclododecene (the saturated product).
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Hydrogenation: a five-membered cycloalkene with H2 (50 psi), PtO2; ether gives the saturated product.