I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
Dicyclopentadiene is used in resins, particularly unsaturated polyester resins. It plays a major role in inks, adhesives and paints. It is also used as a monomer in polymerization reactions. It is a precursor for the preparation of endo-tetrahydrodicyclopentadiene, which reacts with aluminum chloride at higher temperature to give adamantine. It undergoes a retro-Diels-Alder reaction to yield cyclopentadiene, which acts as ligand in inorganic chemistry.
Source, on heating, of monomeric cyclopentadiene. For details, see: Org. Synth. Coll., 7, 339 (1990).
Diels-Alder reaction with 1,4-benzoquinones and subsequent retro Diels-Alder with elimination of cyclopentadiene have been used in synthesis of 2-cyclohexene-1,4-diones: J. Chem. Soc. (C), 124 (1969); Org. Synth. Coll., 9, 186 (1998). For an enantioselective, catalytic Diels-Alder reaction, see: Org. Synth. Coll., 9, 67 (1998).
Readily deprotonated by strong bases to give the 6πAlpha/Delectron cyclopentadienyl anion, which forms stable complexes with many transition metals. Conversion to ferrocene by two alternative procedures: Org. Synth. Coll., 4, 473 (1963), or using crown-ether catalysis: Angew. Chem. Int. Ed., 18, 792 (1979). Preparation of ruthenocene: Org. Synth. Coll., 5, 1001 (1973).
The cyclopentadienyl anion reacts with carbonyl compounds with the formation of fulvenes. For example using KOH and 18-crown-6, see: Synthesis, 799 (1980).
For a review of methods for the synthesis of a wide variety of 1,3-bifunctionalized cyclopentanes and cyclopentenes from cyclopentadiene, see: Angew. Chem. Int. Ed., 21, 480 (1982).
Wang, L.; Ma, Y.; Qing, S.; Gao, Z.; Eli, W.; Wang, T. Magnetically Separable Fe3O4 Supported Co-Rh Bimetallic Catalysts for Dicyclopentadiene Hydroformylation to Value-Added Fine Chemicals. Energy Environ. Focus 2015, 4 (4), 334-339.
Autenrieth, B.; Jeong, H.; Forrest, W. P.; Axtell, J. C.; Ota, A.; Lehr, T.; Buchmeiser, M. R.; Schrock, R. R. Stereospecific Ring-Opening Metathesis Polymerization (ROMP) of endo-Dicyclopentadiene by Molybdenum and Tungsten Catalysts. Macromolecules 2015, 48 (8), 2480-2492.
Hazard Statements: H225-H302-H332-H315-H319-H335
Highly flammable liquid and vapour. Harmful if swallowed. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.