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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Bicyclo[2.2.1]hepta-2,5-diene | |||
| Other names
2,5-Norbornadiene | |||
| Identifiers | |||
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3D model (JSmol) |
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| ChemSpider | |||
| ECHA InfoCard | 100.004.066 
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| EC Number |
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PubChem CID |
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| UNII | |||
| UN number | 2251 | ||
CompTox Dashboard (EPA) |
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| Properties | |||
| C7H8 | |||
| Molar mass | 92.14 g/mol | ||
| Density | 0.906 g/cm3 | ||
| Melting point | −19 °C (−2 °F; 254 K) | ||
| Boiling point | 89 °C (192 °F; 362 K) | ||
| Insoluble | |||
| Hazards | |||
| GHS labelling: | |||
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| Danger | |||
| H225 | |||
| P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
Norbornadiene is an organic compound and a bicyclic hydrocarbon. Norbornadiene is of interest as a metal-binding ligand, whose complexes are useful for homogeneous catalysis. It has been intensively studied owing to its high reactivity and distinctive structural property of being a diene that cannot isomerize (isomers would be anti-Bredt alkenes). Norbornadiene is also a useful dienophileinDiels-Alder reactions.
Norbornadiene can be formed by a Diels-Alder reaction between cyclopentadiene and acetylene[1]
Quadricyclane, a valence isomer, can be obtained from norbornadiene by a photochemical reaction when assisted by a sensitizer such as acetophenone:[2]
The norbornadiene-quadricyclane couple is of potential interest for solar energy storage when controlled release of the strain energy stored in quadricyclane back to norbornadiene is made possible.[3]
Norbornadiene is reactive in cycloaddition reactions. Norbornadiene is also the starting material for the synthesis of diamantane[4] and sumanene and it is used as an acetylene transfer agent for instance in reaction with 3,6-di-2-pyridyl-1,2,4,5-tetrazine.[5]
Norbornadiene is a versatile ligand in organometallic chemistry, where it serves as a two-electron or four-electron donor. (Norbornadiene)molybdenum tetracarbonyl is used as a source of "Mo(CO)4", exploiting the lability of the diene ligand in this case.[6] which is a useful source of "chromium tetracarbonyl," e.g. in reactions with phosphine ligands.
The norbornadiene analogue of cyclooctadiene rhodium chloride dimer has been used in homogeneous catalysis. Chiral, C2-symmetric dienes derived from norbornadiene have also been described.[7][8]
