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| {{Chembox
| | over the counter std test over [http://www.ubi-cation.com/ubication/node/6056 http://www.ubi-cation.com/ubication/node/6056] the counter std test Emilia Shryock is my title but you can call me [http://www.article-galaxy.com/profile.php?a=165109 article-galaxy.com] something you like. He utilized to be unemployed but now he is a computer operator but his [http://stdtestguide.com/std-testing/home-std-test/ marketing] by no means arrives. The preferred hobby for my children and me is to perform baseball but I haven't produced a dime with it. My family members lives home std test in Minnesota and my family loves it.<br><br>my website [http://telekomxchange.com/groups/prevent-infections-before-hand-using-these-tips/ http://telekomxchange.com/groups/prevent-infections-before-hand-using-these-tips/] |
| | Verifiedfields = changed
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| | Watchedfields = changed
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| | verifiedrevid = 477206505
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| | ImageFile = 1,5-Cyclooctadiene.svg
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| | ImageFile_Ref = {{chemboximage|correct|??}}
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| | ImageSize = 100
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| | ImageName = Skeletal formula of 1,5-cyclooctadiene
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| | ImageFile1 = 1,5-cyclooctadiene-ED-3D-balls.png
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| | ImageFile1_Ref = {{chemboximage|correct|??}}
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| | ImageSize1 = 100
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| | ImageName1 = Ball and stick model of 1,5-cyclooctadiene
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| | SystematicName = Cycloocta-1,5-diene<ref>{{Cite web|title = AC1L1QCE - Compound Summary|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8135|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 14 October 2011|location = USA|date = 26 March 2005|at = Identification and Related Records}}</ref>
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| | Section1 = {{Chembox Identifiers
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| | Abbreviations = 1,5-COD
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| | CASNo = 111-78-4
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| | CASNo_Ref = {{cascite|correct|CAS}}
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| | CASNo1 = 1552-12-1
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| | CASNo1_Comment = (''Z'',''Z'')
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| | CASNo2 = 5259-71-2
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| | CASNo2_Comment = (''Z'',''E'')
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| | CASNo3 = 17612-50-9
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| | CASNo3_Comment = (''E'',''E'')
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| | PubChem = 8135
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| | PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
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| | PubChem1 = 82916
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| | PubChem1_Ref = {{Pubchemcite|correct|Pubchem}}
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| | PubChem1_Comment = (''Z'',''Z'')
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| | PubChem2 = 5364364
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| | PubChem2_Ref = {{Pubchemcite|correct|Pubchem}}
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| | PubChem2_Comment = (''Z'',''E'')
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| | PubChem3 = 5702534
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| | PubChem3_Ref = {{Pubchemcite|correct|Pubchem}}
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| | PubChem3_Comment = (''E'',''E'')
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| | ChemSpiderID = 7843
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| | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
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| | ChemSpiderID1 = 74815
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| | ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| |
| | ChemSpiderID1_Comment = (''Z'',''Z'')
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| | ChemSpiderID2 = 18520443
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| | ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
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| | ChemSpiderID2_Comment = (''Z'',''E'')
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| | ChemSpiderID3 = 19971660
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| | ChemSpiderID3_Ref = {{chemspidercite|correct|chemspider}}
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| | ChemSpiderID3_Comment = (''E'',''E'')
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| | EINECS = 203-907-1
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| | UNNumber = 2520
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| | MeSHName = 1,5-cyclooctadiene
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| | RTECS = GX9560000<br />
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| GX9620000 (''Z'',''Z'')
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| | Beilstein = 2036542<br />
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| 1209288 (''Z'',''Z'')
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| | SMILES = C1CC=CCCC=C1
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| | StdInChI = 1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7-
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| | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| | InChI = 1/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7-
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| | StdInChIKey = VYXHVRARDIDEHS-QGTKBVGQSA-N
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| | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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| | InChIKey = VYXHVRARDIDEHS-QGTKBVGQBM
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| }}
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| | Section2 = {{Chembox Properties
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| | C = 8
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| | H = 12
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| | ExactMass = 108.093900384 g mol<sup>-1</sup>
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| | Appearance = Colorless liquid
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| | Density = 0.882 g/mL
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| | MeltingPtK = 204
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| | BoilingPtK = 423
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| | VaporPressure = 910 Pa
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| | RefractIndex = 1.493
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| }}
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| | Section3 = {{Chembox Thermochemistry
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| | DeltaHf = 21-27 kJ mol<sup>-1</sup>
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| | DeltaHc = -4.890--4.884 MJ mol<sup>-1</sup>
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| | Entropy = 250.0 J K<sup>-1</sup> mol<sup>-1</sup>
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| | HeatCapacity = 198.9 J K<sup>-1</sup> mol<sup>-1</sup>
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| }}
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| | Section4 = {{Chembox Hazards
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| | GHSPictograms = {{GHS flame}} {{GHS health hazard}}
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| | GHSSignalWord = '''DANGER'''
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| | HPhrases = {{H-phrases|226|304|315|317|319|334}}
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| | PPhrases = {{P-phrases|261|280|301+310|305+351+338|331|342+311}}
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| | EUClass = {{Hazchem Xn}}
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| | RPhrases = {{R10}}, {{R36/38}}, {{R42/43}}, {{R65}}
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| | SPhrases = {{S23}}, {{S26}}, {{S36/37}}, {{S62}}
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| | FlashPt = 32–38 °C
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| | AutoignitionC = 222
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| }}
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| }}
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| '''1,5-Cyclooctadiene''' is the [[organic compound]] with the chemical formula C<sub>8</sub>H<sub>12</sub>. Generally abbreviated COD, this [[diene]] is a useful precursor to other organic compounds and serves as a [[ligand]] in [[organometallic chemistry]].<ref name="buehler" /><ref name="shriver" />
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| == Synthesis ==
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| 1,5-Cyclooctadiene can be prepared by dimerization of [[butadiene]] in the presence of a nickel catalyst, a coproduct being vinylcyclohexene. Approximately 10,000 tons were produced in 2005.<ref name="thomas" />
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| == Organic reactions ==
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| COD reacts with borane to give [[9-Borabicyclo(3.3.1)nonane|9-borabicyclo[3.3.1]nonane]],<ref name="john" /> commonly known as 9-BBN, a [[reagent]] in organic chemistry used in [[Hydroboration–oxidation reaction|hydroboration]]s:
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| :[[File:Synthesis of 9-BBN dimer.png|450px]]
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| COD adds SCl<sub>2</sub> (or similar reagents) to give 2,6-dichloro-9-thiabicyclo[3.3.1]nonane:<ref name="bishop" />
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| :[[File:CODSCl2.png|450px|2,6-Dichloro-9-thiabicyclo[3.3.1]nonane, synthesis and reactions]]
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| The resulting dichloride can be further modified as the di-[[azide]] or di-[[cyano]] derivative in a [[nucleophilic substitution]] aided by [[anchimeric assistance]].
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| == Metal complexes ==
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| [[File:M(cod)2.png|thumb|240px|left|Structure of M(COD)<sub>2</sub> for M = Ni, Pd, Pt.]]
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| 1,5-COD typically binds to low-valent metals via both alkene groups. The complex [[Nickel bis(cyclooctadiene)|Ni(COD)<sub>2</sub>]] is a precursor to several nickel(0) and Ni(II) complexes. Metal-COD complexes are attractive because they are sufficiently stable to be isolated, often being more robust than related ethylene complexes. The stability of COD complexes is attributable to the [[chelate effect]]. The COD ligands are easily displaced by other ligands, such as phosphines.
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| Ni(COD)<sub>2</sub> is prepared by reduction of [[anhydrous]] nickel [[acetylacetonate]] in the presence of the ligand, using [[triethylaluminium]]
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| <ref name="ittel" />
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| :1/3 [Ni(C<sub>5</sub>H<sub>7</sub>O<sub>2</sub>)<sub>2</sub>]<sub>3</sub> + 2 COD + 2 Al(C<sub>2</sub>H<sub>5</sub>)<sub>3</sub> → Ni(COD)<sub>2</sub> + 2 Al(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>(C<sub>5</sub>H<sub>7</sub>O<sub>2</sub>) + C<sub>2</sub>H<sub>4</sub> + C<sub>2</sub>H<sub>6</sub> | |
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| The related Pt(COD)<sub>2</sub> is prepared by a more circuitous route involving the dilithium [[cyclooctatetraene]]:<ref name="crascall" />
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| :Li<sub>2</sub>C<sub>8</sub>H<sub>8</sub> + PtCl<sub>2</sub>(COD) + 3 C<sub>7</sub>H<sub>10</sub> → [Pt(C<sub>7</sub>H<sub>10</sub>)<sub>3</sub>] + 2 LiCl + C<sub>8</sub>H<sub>8</sub> + C<sub>8</sub>H<sub>12</sub>
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| :Pt(C<sub>7</sub>H<sub>10</sub>)<sub>3</sub> + 2 COD → Pt(COD)<sub>2</sub> + 3 C<sub>7</sub>H<sub>10</sub>
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| Extensive work has been reported on complexes of COD, much of which can has been described in volumes 25, 26, and 28 of ''[[Inorganic Syntheses]]''. The platinum complex has been used in many syntheses:
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| :Pt(COD)<sub>2</sub> + 3 C<sub>2</sub>H<sub>4</sub> → Pt(C<sub>2</sub>H<sub>4</sub>)<sub>3</sub> + 2 COD
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| COD complexes are useful as starting materials, one noteworthy example is the reaction:
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| :Ni(COD)<sub>2</sub> + 4 CO<sub>(g)</sub> <math>\rightleftharpoons</math> Ni(CO)<sub>4</sub> + 2 COD
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| The product Ni(CO)<sub>4</sub> is highly toxic, thus it is advantageous to generate it in the reaction vessel as opposed to being dispensed directly. Other low-valent metal complexes of COD include Mo(COD)(CO)<sub>4</sub>, [RuCl<sub>2</sub>(COD)]<sub>n</sub>, and Fe(COD)(CO)<sub>3</sub>. COD is an especially important in the coordination chemistry of rhodium(I) and iridium(I), examples being [[Crabtree's catalyst]] and [[cyclooctadiene rhodium chloride dimer]].
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| The M(cod)<sub>2</sub> complexes with nickel, palladium, and platinum have [[Tetrahedral molecular geometry|tetrahedral geometry]], whereas [M(COD)<sub>2</sub>]<sup>+</sup> complexes of rhodium and iridium are [[Square planar molecular geometry|square planar]].
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| ==(''E'',''E'')-COD==
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| [[File:EE-COD synthesis.svg|thumb|600px|center|E,E-COD synthesis (Stöckmann et al. 2011)]]
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| The highly strained [[Cis–trans isomerism|''trans''-''trans'' isomer]] of 1,5-cyclooctadiene is a known compound. (''E'',''E'')-COD was first synthesized by [[George M. Whitesides|Whitesides]] and [[Arthur C. Cope|Cope]] in 1969 by [[photoisomerization]] of the ''cis'' compound.<ref>{{cite journal | title = Irradiation of cis,cis-1,5-cyclooctadiene in the presence of copper(I) chloride | author1= [[George M. Whitesides]] | author2 = Gerald L. Goe | author3= [[Arthur C. Cope]] | journal = J. Am. Chem. Soc. | year = 1969 | volume = 91 | issue = 10 | pages = 2608–2616 | doi = 10.1021/ja01038a036}}</ref> Another synthesis (double elimination reaction from a cyclooctane ring) was reported by [[Rolf Huisgen|Huisgen]] in 1987.<ref>{{cite journal | title = Preparation and conformation of (E,E)-1,5-cyclooctadiene | author1 = Dieter Boeckh | author2 = [[Rolf Huisgen]] | author3 = Heinrich Noeth | journal = J. Am. Chem. Soc. | year = 1987 | volume = 109 | issue = 4 | pages = 1248–1249 | doi = 10.1021/ja00238a046}}</ref> The [[molecular conformation]] of (''E'',''E'')-COD is twisted rather than chair-like. The compound has been investigated as a [[click chemistry]] mediator.<ref>{{cite journal | title = (E,E)-1,5-Cyclooctadiene: a small and fast click-chemistry multitalent | author1 = Henning Stöckmann | author2 = André A. Neves | author3 = Henry A. Day | author4 = Shaun Stairs | author5 = Kevin M. Brindle | author6 = Finian J. Leeper | journal = Chem. Commun. | year = 2011 | doi = 10.1039/C1CC12161H}}</ref>
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| ==References==
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| {{Reflist|refs=
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| <ref name="buehler">{{cite book | author1 = Buehler, C | author2 = Pearson, D. | title = Survey of Organic Syntheses | publisher = Wiley-Intersciene | location = New York | year = 1970}}</ref>
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| <ref name="shriver">{{cite book | author1 = Shriver, D | author2 = Atkins, P. | title = Inorganic Chemistry | publisher = W. H. Freeman and Co. | location = New York | year = 1999}}</ref>
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| <ref name="john">{{OrgSynth | collvol = 9 | collvolpages = 95 | year= 1998 | title = <nowiki>9-Borabicyclo[3.3.1]nonane Dimer</nowiki> | author = John A. Soderquist and Alvin Negron | prep = cv9p0095}}</ref>
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| <ref name="bishop">{{OrgSynth | author = Roger Bishop | collvol = 9 | collvolpages = 692 | prep = CV9P0692| title = <nowiki>9-Thiabicyclo[3.3.1]nonane-2,6-dione</nowiki>}}{{cite journal | title = <nowiki>2,6-Dichloro-9-thiabicyclo[3.3.1]nonane:</nowiki> Multigram Display of Azide and Cyanide Components on a Versatile Scaffold | journal = [[Molecules (journal)|Molecules]] | year = 2006 | volume = 11 | pages = 212–218 | url = http://www.mdpi.org/molecules/papers/11040212.pdf | doi = 10.3390/11040212 | author = Díaz, David Díaz | last2 = Converso | first2 = Antonella | last3 = Sharpless | first3 = K. Barry | last4 = Finn | first4 = M. G. | issue = 4}}</ref>
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| <ref name="ittel">{{cite journal | author = Schunn, R; Ittel, S. | title = Bis(1,5-Cyclooctadiene) Nickel(0) | journal = [[Inorg. Synth.]] | volume = 28 | year = 1990 | doi = 10.1002/9780470132593.ch25 | pages = 94 | series = Inorganic Syntheses | isbn = 978-0-470-13259-3}}</ref>
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| <ref name="thomas">Thomas Schiffer, Georg Oenbrink “Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene” in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.</ref>
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| <ref name="crascall">{{cite journal | author = Crascall, L; Spencer, J. | doi = 10.1002/9780470132593.ch34 | journal = [[Inorg. Synth.]] | year = 1990 | volume = 28 | title = Olefin Complexes of Platinum | pages = 126 | series = Inorganic Syntheses | isbn = 978-0-470-13259-3}}</ref>
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| }}
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| {{cycloalkenes}}
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| {{DEFAULTSORT:Cyclooctadiene, 1,5-}}
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| [[Category:Cycloalkenes]]
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| [[Category:Cod complexes|*]]
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| [[Category:Dienes]]
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