1,1-Bis(chloromethyl)ethylene explained

1,1-Bis(chloromethyl)ethylene is the organic compound with the formula CH2=C(CH2Cl)2. It is a colorless liquid. Featuring two allylic chloride substituents, it is dialkylating agent.

Synthesis and reactions

It is prepared from pentaerythritol via a multistep procedure, beginning with the partial chlorination.[1] [2] The compound reacts with diiron nonacarbonyl to give the complex of trimethylenemethane Fe(η4-C(CH2)3)(CO)3. It is also a precursor to [1.1.1]-propellane.

Notes and References

  1. Improved Preparations of 3-Chloro-2-(chloromethyl)-1-propene and 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane: Intermediates in the Synthesis of [1.1.1]Propellane. Mondanaro Lynch. Kathleen. Dailey. William P.. Journal of Organic Chemistry. 1995. 60. 14 . 4666-8. 10.1021/jo00119a057.
  2. Mondanaro . Kathleen R. . Dailey . William P . 3-CHLORO-2-(CHLOROMETHYL)-1-PROPENE . Organic Syntheses . 1998 . 75 . 89 . 10.15227/orgsyn.075.0089.

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