Menu
Home
People
Places
Arts
History
Plants & Animals
Science
Life & Culture
Technology
Reference.org
1,5-Cyclooctadiene
open-in-new
<p>1,5-Cyclooctadiene (also known as cycloocta-1,5-diene) is a <a href="/facts/Cyclic_compound/TH2ReKIQ">cyclic</a> <a href="/facts/Hydrocarbon/Dcg95Ju5">hydrocarbon</a> with the chemical formula C8H12, specifically [−(CH2)2−CH=CH−]2. </p><p>There are three <a href="/facts/Configurational_isomer/I3kzlDE8">configurational isomers</a> with this structure, that differ by the arrangement of the four C–C single bonds adjacent to the double bonds. Each pair of single bonds can be on the same side (<i>cis</i>,<i>Z</i>) or on opposite sides (<i>trans</i>,<i>E</i>) of the double bond's plane; the three possibilities are denoted <i>cis,cis</i>, <i>trans,trans</i>, and <i>cis,trans</i>; or (<i>Z,Z</i>), (<i>E,E</i>), and (<i>Z,E</i>). (Because of overall symmetry, <i>trans,cis</i> is the same configuration as <i>cis,trans</i>.) </p><p>Generally abbreviated COD, the <i>cis,cis</i> isomer of this <a href="/facts/Diene/F5NxrLPW">diene</a> is a useful precursor to other organic compounds and serves as a <a href="/facts/Ligand/6etB3qeW">ligand</a> in <a href="/facts/Organometallic_chemistry/bhqFz2P0">organometallic chemistry</a>. It is a colorless liquid with a strong odor. 1,5-Cyclooctadiene can be prepared by dimerization of <a href="/facts/Butadiene/j9W2LxGv">butadiene</a> in the presence of a nickel catalyst, a coproduct being <a href="/facts/4-Vinylcyclohexene/UEFgDv2l">vinylcyclohexene</a>. Approximately 10,000 tons were produced in 2005. </p>