page_title: Butadiene
section_title: Reactions
hierarchical_section_title: Butadiene / Reactions
caption_attribution_description: English: Fe(butadiene)(CO)3 from Xray
context_page_description: 1,3-Butadiene is the organic compound with the formula (CH₂=CH)₂. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a monomer in the production of synthetic rubber. The molecule can be viewed as the union of two vinyl groups. It is the simplest conjugated diene.
  Although butadiene breaks down quickly in the atmosphere, it is nevertheless found in ambient air in urban and suburban areas as a consequence of its constant emission from motor vehicles.
  The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene with structure H₂C=C=CH−CH₃. This allene has no industrial significance.
context_section_description: The industrial uses illustrate the tendency of butadiene to polymerize.  Its susceptibility to 1,4-addition reactions is illustrated by it hydrocyanation.  Like many dienes, it undergoes Pd-catalyzed reactions that proceed via allyl complexes.  It is a partner in Diels-Alder reactions, e.g. with maleic anhydride to give tetrahydrophthalic anhydride.
  Like other dienes, butadiene is a ligand for low-valent metal complexes, e.g. the derivatives Fe(butadiene)(CO)₃ and Mo(butadiene)₃.
caption: The structure of (butadiene)iron tricarbonyl.[23]
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