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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:

2CH<sub>2</sub>=CHCN + 2e<sup>−</sup> + 2H<sup>+</sup> → NCCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CN

The reaction applies to a number electrophilic alkenes (Michael acceptors).

References