Norbornadiene

Norbornadiene
Names
	Preferred IUPAC name Bicyclo[2.2.1]hepta-2,5-diene
	Other names 2,5-Norbornadiene
Identifiers
CAS Number	121-46-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	8160;
ECHA InfoCard	100.004.066
EC Number	204-472-0;
PubChem CID	8473;
UNII	W9ZTQ75ZUS ;
UN number	2251
CompTox Dashboard (EPA)	DTXSID1059523 ;
	InChI InChI=1S/C7H8/c1-2-7-4-3-6(1)5-7/h1-4,6-7H,5H2 Key: SJYNFBVQFBRSIB-UHFFFAOYSA-N;
	SMILES C1C2C=CC1C=C2;
Properties
Chemical formula	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)
Solubility in water	Insoluble
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225
Precautionary statements	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). verify (what is ?) Infobox references

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 dienophile in Diels-Alder reactions.

Synthesis

Norbornadiene can be formed by a Diels-Alder reaction between cyclopentadiene and acetylene^[1]

Reactions

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]

As a ligand

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]

References

^ Orrego‐Hernández, Jessica; Hölzel, Helen; Quant, Maria; Wang, Zhihang; Moth‐Poulsen, Kasper (2021-10-14). "Scalable Synthesis of Norbornadienes via in situ Cracking of Dicyclopentadiene Using Continuous Flow Chemistry". European Journal of Organic Chemistry. 2021 (38): 5337–5342. doi:10.1002/ejoc.202100795. ISSN 1434-193X.
^ Smith, Claiborune D. (1988). "Quadricyclane". Organic Syntheses; Collected Volumes, vol. 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. Bibcode:1997JPCA..101.8834S. 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 Archived 2012-07-28 at the Wayback Machine
^ 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. PMC 6236418. S2CID 53874105.
^ 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.
^ Ryo Shintani, Tamio Hayashi "Chiral Diene Ligands for Asymmetric Catalysis" Aldrich Chimica Acta 2009, vol. 42, number 2, pp. 31-38.
^ Huang, Yinhua; Hayashi, Tamio (2022). "Chiral Diene Ligands in Asymmetric Catalysis". Chemical Reviews. 122 (18): 14346–14404. doi:10.1021/acs.chemrev.2c00218. PMID 35972018.

[1] Orrego‐Hernández, Jessica; Hölzel, Helen; Quant, Maria; Wang, Zhihang; Moth‐Poulsen, Kasper (2021-10-14). "Scalable Synthesis of Norbornadienes via in situ Cracking of Dicyclopentadiene Using Continuous Flow Chemistry". European Journal of Organic Chemistry. 2021 (38): 5337–5342. doi:10.1002/ejoc.202100795. ISSN 1434-193X.

[2] Smith, Claiborune D. (1988). "Quadricyclane". Organic Syntheses; Collected Volumes, vol. 6, p. 962.

[3] 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. Bibcode:1997JPCA..101.8834S. CiteSeerX 10.1.1.130.1791. doi:10.1021/jp972007h.

[4] Diamantane in Organic Syntheses Coll. Vol. 6, p.378; Vol. 53, p.30 Online Article Archived 2012-07-28 at the Wayback Machine

[5] 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. PMC 6236418. S2CID 53874105.

[6] 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.

[7] Ryo Shintani, Tamio Hayashi "Chiral Diene Ligands for Asymmetric Catalysis" Aldrich Chimica Acta 2009, vol. 42, number 2, pp. 31-38.

[8] Huang, Yinhua; Hayashi, Tamio (2022). "Chiral Diene Ligands in Asymmetric Catalysis". Chemical Reviews. 122 (18): 14346–14404. doi:10.1021/acs.chemrev.2c00218. PMID 35972018.

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Norbornadiene

Synthesis

Reactions

As a ligand

See also

References

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