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]
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Production of Acrylonitrile (A147487)
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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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This page was last edited on 18 July 2023, at 18:30