Norbornadiene: Difference between revisions

| verifiedrevid = 307089458

| ImageFile = norbornadiene.png

| ImageSize = 150px

| ImageFileL1 = norbornadiene2.png

| ImageSizeL1 = 100px

| ImageFileR1 = norbornadiene3.png

| ImageSizeR1 = 100px

| IUPACName = Bicyclo[2.2.1]hepta-2,5-diene

| OtherNames = 2,5-Norbornadiene

| Section1 = {{Chembox Identifiers

| Abbreviations =

| CASNo_Ref = {{cascite}}

| CASNo = 121-46-0

| EINECS = 204-472-0

| PubChem = 8473

| SMILES = C1C2C=CC1C=C2

| InChI =

| RTECS =

| MeSHName =

| ChEBI =

| KEGG =

| ATCCode_prefix =

| ATCCode_suffix =

| ATC_Supplemental =}}

| Section2 = {{Chembox Properties

| Formula = C₇H₈

| MolarMass = 92.14 g/mol

| Appearance =

| Density = 0.906 g/cm³

| MeltingPtC = -19

| Melting_notes =

| BoilingPtC = 89

| Boiling_notes =

| Solubility = Insoluble

| SolubleOther =

| Solvent =

| pKa =

| pKb = }}

| Section7 = {{Chembox Hazards

| EUClass =

| EUIndex =

| MainHazards =

| NFPA-H =

| NFPA-F =

| NFPA-R =

| NFPA-O =

| RPhrases = {{R11}}

| SPhrases = {{S9}} {{S16}} {{S29}} {{S33}}

| RSPhrases =

| FlashPt =

| Autoignition =

| ExploLimits =

| PEL = }}

'''Norbornadiene''' is an [[organic compound]]. This bicyclic [[hydrocarbon]] is the most stable diolefin derived from the norbornane and [[norbornene]]. Norbornadiene is primarily of interest as a [[ligand]] in [[homogeneous catalysis]], but it has been heavily studied due to its high reactivity and distinctive structural property of being a [[diene]] that cannot isomerize.

Norbornadiene forms via the [[Diels-Alder reaction]] between a [[cyclopentadiene]] and an [[alkyne]].

:[[Image:Norbornadiene synthesis.gif|left|Norbornadiene synthesis]]<br style="clear:left;"/>

[[Quadricyclane]], a valence [[isomer]], can be obtained from norbornadiene by a [[photochemical reaction]] when assisted by a [[photochemical sensitizer|sensitizer]] such as [[acetophenone]]:<ref>{{OrgSynth | author = Smith, Claiborune D. | title = Quadricyclane | prep = cv6p0962 | collvol = 6 | collvolpages = 962 | year = 1988}}</ref>

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.<ref>{{cite journal | title = Rh(III)-Photosensitized Interconversion of Norbornadiene and Quadricyclane | author = Gregory W. Sluggett, Nicholas J. Turro, and Heinz D. Roth | journal = [[J. Phys. Chem. A]] | year = 1997 | volume = 101 | pages = 8834–8838 | doi = 10.1021/jp972007h}}</ref>

Norbornadiene is reactive in [[cycloaddition]] reactions. Norbornadiene is also the starting material for the synthesis of [[diamantane]]<ref>Diamantane in [[Organic Syntheses]] Coll. Vol. 6, p.378; Vol. 53, p.30 [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv6p0378 Online Article]</ref> 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]].<ref>{{cite journal | title = 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 | author = Ronald N. Warrener and Peter A. Harrison | journal = [[Molecules (journal)|Molecules]] | year = 2001 | volume = 6 | pages = 353–369 | url = http://www.mdpi.org/molecules/papers/60400353.pdf | doi = 10.3390/60400353}}</ref>

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]]. Chiral, ''C''₂-symmetric dienes derived from norbornadiene have also been described.<ref>Ryo Shintani, Tamio Hayashi "Chiral Diene Ligands for Asymmetric Catalysis" Aldrich Chimica Acta 2009, vol. 42, number 2, pp. 31-38.</ref>

One example is tetracarbonyl(norbornadiene)chromium(0),<ref>{{cite journal | title = High yield synthesis and structures of some achiral and chiral (diphosphine)tetracarbonylchromium(0) chelate complexes with tetracarbonyl(norbornadiene)chromium(0) as complexation reagent | author = Markus Strotmann, Rudolf Wartchow, and Holger Butenschön | journal = [[Arkivoc]] | pages = KK–1112F | year = 2004 | url = http://www.arkat-usa.org/ark/journal/2004/I13_Krohn/1112/KK-1112F.asp }}</ref> which is a useful source of "[[Chromium carbonyl|chromium tetracarbonyl]]," e.g. in reactions with phosphine [[ligand]]s.

[[fr:Norbornadiène]]

[[nl:Norbornadieen]]

[[ja:ノルボルナジエン]]