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m WP:CHECKWIKI error fixes (22) using AWB (9842)
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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
| Watchedfields = changed
| verifiedrevid = 477206505
| ImageFile = 1,5-Cyclooctadiene.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 100
| ImageName = Skeletal formula of 1,5-cyclooctadiene
| ImageFile1 = 1,5-cyclooctadiene-ED-3D-balls.png
| ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageSize1 = 100
| ImageName1 = Ball and stick model of 1,5-cyclooctadiene
| 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>
| Section1 = {{Chembox Identifiers
|  Abbreviations = 1,5-COD
|  CASNo = 111-78-4
|  CASNo_Ref = {{cascite|correct|CAS}}
|  CASNo1 = 1552-12-1
|  CASNo1_Comment = (''Z'',''Z'')
|  CASNo2 = 5259-71-2
|  CASNo2_Comment =  (''Z'',''E'')
|  CASNo3 = 17612-50-9
|  CASNo3_Comment =  (''E'',''E'')
|  PubChem = 8135
|  PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
|  PubChem1 = 82916
|  PubChem1_Ref = {{Pubchemcite|correct|Pubchem}}
|  PubChem1_Comment =  (''Z'',''Z'')
|  PubChem2 = 5364364
|  PubChem2_Ref = {{Pubchemcite|correct|Pubchem}}
|  PubChem2_Comment =  (''Z'',''E'')
|  PubChem3 = 5702534
|  PubChem3_Ref = {{Pubchemcite|correct|Pubchem}}
|  PubChem3_Comment =  (''E'',''E'')
|  ChemSpiderID = 7843
|  ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
|  ChemSpiderID1 = 74815
|  ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
|  ChemSpiderID1_Comment =  (''Z'',''Z'')
|  ChemSpiderID2 = 18520443
|  ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
|  ChemSpiderID2_Comment =  (''Z'',''E'')
|  ChemSpiderID3 = 19971660
|  ChemSpiderID3_Ref = {{chemspidercite|correct|chemspider}}
|  ChemSpiderID3_Comment =  (''E'',''E'')
|  EINECS = 203-907-1
|  UNNumber = 2520
|  MeSHName = 1,5-cyclooctadiene
|  RTECS = GX9560000<br />
GX9620000  (''Z'',''Z'')
|  Beilstein = 2036542<br />
1209288  (''Z'',''Z'')
|  SMILES = C1CC=CCCC=C1
|  StdInChI = 1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7-
|  StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|  InChI = 1/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7-
|  StdInChIKey = VYXHVRARDIDEHS-QGTKBVGQSA-N
|  StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|  InChIKey = VYXHVRARDIDEHS-QGTKBVGQBM
}}
| Section2 = {{Chembox Properties
|  C = 8
|  H = 12
|  ExactMass = 108.093900384 g mol<sup>-1</sup>
|  Appearance = Colorless liquid
|  Density = 0.882 g/mL
|  MeltingPtK = 204
|  BoilingPtK = 423
|  VaporPressure = 910 Pa
|  RefractIndex = 1.493
}}
| Section3 = {{Chembox Thermochemistry
|  DeltaHf = 21-27 kJ mol<sup>-1</sup>
|  DeltaHc = -4.890--4.884 MJ mol<sup>-1</sup>
|  Entropy = 250.0 J K<sup>-1</sup> mol<sup>-1</sup>
|  HeatCapacity = 198.9 J K<sup>-1</sup> mol<sup>-1</sup>
}}
| Section4 = {{Chembox Hazards
|  GHSPictograms = {{GHS flame}} {{GHS health hazard}}
|  GHSSignalWord = '''DANGER'''
|  HPhrases = {{H-phrases|226|304|315|317|319|334}}
|  PPhrases = {{P-phrases|261|280|301+310|305+351+338|331|342+311}}
|  EUClass = {{Hazchem Xn}}
|  RPhrases = {{R10}}, {{R36/38}}, {{R42/43}}, {{R65}}
|  SPhrases = {{S23}}, {{S26}}, {{S36/37}}, {{S62}}
|  FlashPt = 32–38&nbsp;°C
|  AutoignitionC = 222
}}
}}
 
'''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" />
 
== Synthesis ==
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" />
 
== Organic reactions ==
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:
:[[File:Synthesis of 9-BBN dimer.png|450px]]
 
COD adds SCl<sub>2</sub> (or similar reagents) to give 2,6-dichloro-9-thiabicyclo[3.3.1]nonane:<ref name="bishop" />
:[[File:CODSCl2.png|450px|2,6-Dichloro-9-thiabicyclo[3.3.1]nonane, synthesis and reactions]]
 
The resulting dichloride can be further modified as the di-[[azide]] or di-[[cyano]] derivative in a [[nucleophilic substitution]] aided by [[anchimeric assistance]].
 
== Metal complexes ==
[[File:M(cod)2.png|thumb|240px|left|Structure of M(COD)<sub>2</sub> for M = Ni, Pd, Pt.]]
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.
 
Ni(COD)<sub>2</sub> is prepared by reduction of [[anhydrous]] nickel [[acetylacetonate]] in the presence of the ligand, using [[triethylaluminium]]
<ref name="ittel" />
: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>
 
The related Pt(COD)<sub>2</sub> is prepared by a more circuitous route involving the dilithium [[cyclooctatetraene]]:<ref name="crascall" />
: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>
: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>
 
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:
: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
 
COD complexes are useful as starting materials, one noteworthy example is the reaction:
:Ni(COD)<sub>2</sub>  +  4 CO<sub>(g)</sub> <math>\rightleftharpoons</math> Ni(CO)<sub>4</sub>  +  2 COD
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 directlyOther 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]].
 
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]].
 
==(''E'',''E'')-COD==
[[File:EE-COD synthesis.svg|thumb|600px|center|E,E-COD synthesis (Stöckmann et al. 2011)]]
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>
 
==References==
{{Reflist|refs=
<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>
<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>
<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>
<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>
<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>
<ref name="thomas">Thomas Schiffer, Georg Oenbrink “Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene” in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.</ref>
<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>
}}
 
{{cycloalkenes}}
 
{{DEFAULTSORT:Cyclooctadiene, 1,5-}}
[[Category:Cycloalkenes]]
[[Category:Cod complexes|*]]
[[Category:Dienes]]

Latest revision as of 20:38, 25 December 2014

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