Hydrodimerization

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]

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

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

References

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

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[1] Baizer, Manuel M. (1964). "Electrolytic Reductive Coupling". Journal of the Electrochemical Society. 111 (2): 215. doi:10.1149/1.2426086.

[2] White, D. A. (1981). "Electrohydrodimerization of an Activated Alkene: Tetraethyl 1,2,3,4-Butanetetracarboxylate". Org. Synth. 60: 58. doi:10.15227/orgsyn.060.0058.

[3] Knunyants, I. L.; Vyazankin, N. S. (1957). "Reductive dimerization of derivatives of α,β-unsaturated acids". Doklady Akademii Nauk SSSR. 113: 112–15.