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:{{cite journal|doi=10.1149/1.2426086|title=Electrolytic Reductive Coupling|journal=Journal of the Electrochemical Society|volume=111|issue=2|pages=215|year=1964|last1=Baizer|first1=Manuel M.}}

:2{{nbsp}}CH₂=CHCN + 2{{nbsp}}e⁻ + 2{{nbsp}}H⁺ → NCCH₂CH₂CH₂CH₂CN

:Image:AdiponitrileSynthesis.png

The reaction applies to a number electrophilic alkenes (Michael acceptors).{{cite journal|title=Electrohydrodimerization of an Activated Alkene: Tetraethyl 1,2,3,4-Butanetetracarboxylate|first1=D. A. |last1=White

|journal=Org. Synth.|year=1981|volume=60|page=58|doi=10.15227/orgsyn.060.0058}}{{cite journal|title=Reductive dimerization of derivatives of α,β-unsaturated acids|last1=Knunyants|first1=I. L.|last2=Vyazankin|first2=N. S.

|journal=Doklady Akademii Nauk SSSR|year=1957|volume=113|pages=112–15}}