Oxymercuration–demercuration

5 real reactions from the literature, on trisubstituted six-membered cycloalkenes, terminal alkynes, styrenes and α,β-unsaturated esters. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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1. Oxymercuration: 1-methylcyclohexene (a trisubstituted six-membered cycloalkene) with 1) Hg(OAc)2, H2O, ether; Hg0; 2) NaBH4, H2O, ether, NaOH gives 1-methylcyclohexanol (the tertiary alcohol).

   OxymercurationOrg. Synth. Coll. Vol. 6, p. 766

2. Oxymercuration: 4-pentynoic acid (a terminal alkyne) with 1); Hg(OAc)2; CH2Cl2; 2); NaBH4 gives 5-methylideneoxolan-2-one (the Markovnikov addition product).

   OxymercurationTetrahedron 2015, 71, 8637

3. Oxymercuration: isobutenylbenzene (a styrene) with (±) gives the ether.

   OxymercurationCan. J. Chem. 1952, 30, 541

4. Oxymercuration: methyl acrylate (an α,β-unsaturated ester) with Hg(OAc)2; CH3OH gives the ether.

   OxymercurationOrg. Synth. Coll. Vol. 3, p. 774

5. Oxymercuration: 1-pentene (a terminal alkene) with 1); 2) gives 2-pentanol (the secondary alcohol).

   OxymercurationJ. Org. Chem. 1970, 35, 1844