| 词条 | Norbornadiene |
| 释义 |
| Watchedfields = changed | verifiedrevid = 404998665 | ImageFile = norbornadiene.png | ImageSize = 150px | ImageFileL1 = norbornadiene2.png | ImageFileR1 = norbornadiene3.png | IUPACName = Bicyclo[2.2.1]hepta-2,5-diene | OtherNames = 2,5-Norbornadiene |Section1={{Chembox Identifiers | Abbreviations = | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 121-46-0 | EINECS = 204-472-0 | PubChem = 8473 | SMILES = C1C2C=CC1C=C2 | InChI = | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = }} |Section2={{Chembox Properties | Formula = C7H8 | MolarMass = 92.14 g/mol | Appearance = | Density = 0.906 g/cm3 | MeltingPtC = -19 | MeltingPt_notes = | BoilingPtC = 89 | BoilingPt_notes = | Solubility = Insoluble | SolubleOther = | Solvent = | pKa = | pKb = }} |Section7={{Chembox Hazards | EUClass = | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | RPhrases = {{R11}} | SPhrases = {{S9}} {{S16}} {{S29}} {{S33}} | RSPhrases = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = }} }} 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. SynthesisNorbornadiene can be formed by a Diels-Alder reaction between cyclopentadiene and acetylene. {{clear|left}}ReactionsQuadricyclane, a valence isomer, can be obtained from norbornadiene by a photochemical reaction when assisted by a sensitizer such as acetophenone:[1]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.[2] Norbornadiene is reactive in cycloaddition reactions. Norbornadiene is also the starting material for the synthesis of diamantane[3] 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.[4] As a ligandNorbornadiene 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, C2-symmetric dienes derived from norbornadiene have also been described.[5] One example is tetracarbonyl(norbornadiene)chromium(0),[6] which is a useful source of "chromium tetracarbonyl," e.g. in reactions with phosphine ligands. See also
References1. ^{{OrgSynth | author = Smith, Claiborune D. | title = Quadricyclane | prep = cv6p0962 | collvol = 6 | collvolpages = 962 | year = 1988}} 2. ^{{cite journal | title = Rh(III)-Photosensitized Interconversion of Norbornadiene and Quadricyclane |author1=Gregory W. Sluggett |author2=Nicholas J. Turro |author3=Heinz D. Roth |last-author-amp=yes | journal = J. Phys. Chem. A | year = 1997 | volume = 101 | pages = 8834–8838 | doi = 10.1021/jp972007h | issue = 47|citeseerx=10.1.1.130.1791 }} 3. ^Diamantane in Organic Syntheses Coll. Vol. 6, p.378; Vol. 53, p.30 Online Article 4. ^{{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 |author1=Ronald N. Warrener |author2=Peter A. Harrison |lastauthoramp=yes | journal = Molecules | year = 2001 | volume = 6 | pages = 353–369 | url = http://www.mdpi.org/molecules/papers/60400353.pdf | doi = 10.3390/60400353 | issue = 4}} 5. ^Ryo Shintani, Tamio Hayashi "Chiral Diene Ligands for Asymmetric Catalysis" Aldrich Chimica Acta 2009, vol. 42, number 2, pp. 31-38. 6. ^{{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 |author1=Markus Strotmann |author2=Rudolf Wartchow |author3=Holger Butenschön |last-author-amp=yes | journal = Arkivoc | pages = KK–1112F | year = 2004 | url = http://www.arkat-usa.org/ark/journal/2004/I13_Krohn/1112/KK-1112F.asp }} 3 : Dienes|Bicyclic compounds|Cyclopentenes |
| 随便看 |
|
开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。