3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||92.14 g/mol|
|Melting point||−19 °C (−2 °F; 254 K)|
|Boiling point||89 °C (192 °F; 362 K)|
|S-phrases (outdated)||S9 S16 S29 S33|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Norbornadiene is a bicyclic hydrocarbon and an organic compound. 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 olefins). Norbornadiene is also a useful dienophile in Diels-Alder reactions.
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.
Norbornadiene is reactive in cycloaddition reactions. Norbornadiene is also the starting material for the synthesis of diamantane 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.
As a ligand
Norbornadiene is a versatile ligand in organometallic chemistry, where it serves as a two-electron or four-electron donor. The norbornadiene analogue of cyclooctadiene rhodium chloride dimer is widely used in homogeneous catalysis. (Norbornadiene)molybdenum tetracarbonyl is used as a source of "Mo(CO)4", exploiting the lability of the diene ligand in this case.
Chiral, C2-symmetric dienes derived from norbornadiene have also been described. One example is tetracarbonyl(norbornadiene)chromium(0), which is a useful source of "chromium tetracarbonyl," e.g. in reactions with phosphine ligands.
- Norbornane a saturated compound with the same carbon skeleton.
- Norbornene a compound with the carbon same skeleton, but with one less double bond.
- Smith, Claiborune D. (1988). "Quadricyclane". Organic Syntheses.; Collective Volume, 6, p. 962
- Gregory W. Sluggett; Nicholas J. Turro & Heinz D. Roth (1997). "Rh(III)-Photosensitized Interconversion of Norbornadiene and Quadricyclane". J. Phys. Chem. A. 101 (47): 8834–8838. CiteSeerX 10.1.1.130.1791. doi:10.1021/jp972007h.
- Diamantane in Organic Syntheses Coll. Vol. 6, p.378; Vol. 53, p.30 Online Article
- Ronald N. Warrener & Peter A. Harrison (2001). "π-Bond Screening in Benzonorbornadienes: The Role of 7-Substituents in Governing the Facial Selectivity for the Diels-Alder Reaction of Benzonorbornadienes with 3,6-Di(2-pyridyl)-s-Tetrazine" (PDF). Molecules. 6 (4): 353–369. doi:10.3390/60400353.
- Ryo Shintani, Tamio Hayashi "Chiral Diene Ligands for Asymmetric Catalysis" Aldrich Chimica Acta 2009, vol. 42, number 2, pp. 31-38.
- Markus Strotmann; Rudolf Wartchow & Holger Butenschön (2004). "High yield synthesis and structures of some achiral and chiral (diphosphine)tetracarbonylchromium(0) chelate complexes with tetracarbonyl(norbornadiene)chromium(0) as complexation reagent". Arkivoc: KK–1112F.