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]