Hydrodimerization Explained

Hydrodimerization is an organic reaction that couples two alkenes to give a symmetrical hydrocarbon. The reaction is often implemented electrochemically; in that case the reaction is called electrodimerization. The reaction can also be induced with samarium diiodide, a one-electron reductant.

Hydrodimerization is the basis of the Monsanto adiponitrile synthesis:^[1]

2CH₂=CHCN + 2e⁻ + 2H⁺ → NCCH₂CH₂CH₂CH₂CN

The reaction applies to a number electrophilic alkenes (Michael acceptors).^{[2] [3]}

References

1. 10.1149/1.2426086. Electrolytic Reductive Coupling. Journal of the Electrochemical Society. 111. 2. 215. 1964. Baizer. Manuel M..
2. Electrohydrodimerization of an Activated Alkene: Tetraethyl 1,2,3,4-Butanetetracarboxylate. D. A. . White. Org. Synth.. 1981. 60. 58. 10.15227/orgsyn.060.0058.
3. Reductive dimerization of derivatives of α,β-unsaturated acids. Knunyants. I. L.. Vyazankin. N. S.. Doklady Akademii Nauk SSSR. 1957. 113. 112–15.