835 4 MeSHName 1,3 cyclopentadiene ChEBI 30664 ChEBI Ref ebicite correct EBI RTECS GY1000000 Beilstein ... MolShape Planar ref cite journal title Ab initio G2 and DFT calculations on electron affinity of cyclopentadiene ... Cyclopentadiene is an organic compound with the Chemical formula formula C sub 5 sub ... Science Books New York, 2010. ISBN 189138953X. ref Production and reactions Cyclopentadiene ... name Ullmann To obtain cyclopentadiene monomer, commercial dicyclopentadiene is cracked by heating ... title Cyclopentadiene and 3 Chlorocyclopentene prep cv4p0238 collvol 4 collvolpages 238 author Robert Bruce Moffett year 1962 ref Sigmatropic rearrangement The hydrogen atoms in cyclopentadiene undergo ... Hall. ref Diels Alder reactions Famously, cyclopentadiene dimerizes via a reversible Diels Alder ... at 20 C. ref name Ullmann Dieter H nicke, Ringo F disch, Peter Claus, Michael Olson Cyclopentadiene ... center 0.5 0 align center 3.5 25 align center 15 40 Cyclopentadiene readily undergoes other Diels ... cyclopentadiene in THF . ref cite book last1 Jolly first1 W. L. title The Synthesis and Characterization ... 2 NaCl Organometallic complexes that include both the cyclopentadienyl anion and cyclopentadiene itself ... Uses Cyclopentadiene is mainly useful as a precursor to cyclopentene and related monomers such as ethylidenenorbornene ... of cyclopentadiene in step 1 to dihydrofulvalene. Abbreviation The commonly used abbreviation ... sv Cyklopentadien ur Cyclopentadiene zh ... more details
DISPLAYTITLE C sub 5 sub H sub 6 sub The molecular formula C sub 5 sub H sub 6 sub may refer to Cyclopentadiene Propellane 1.1.1 propellane MolFormDisambig fr C5H6 ... more details
Dieter H nicke, Ringo F disch, Peter Claus, Michael Olson Cyclopentadiene and Cyclopentene Ullmann ... allyl bromide chlordane from cyclopentadiene , followed by chlorination endrin from acetylene , followed by cyclopentadiene, followed by epoxidation heptachlor from cyclopentadiene, followed by monochlorination ... more details
chembox verifiedrevid 443829334 ImageFileL1 Fulvene.png ImageSizeL1 120px ImageFileR1 Fulvene 3D.png ImageSizeR1 120px IUPACName Fulvene OtherNames 5 Methylene 1,3 cyclopentadiene Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 120097 InChI 1 C6H6 c1 6 4 2 3 5 6 h2 5H,1H2 InChIKey PGTKVMVZBBZCKQ UHFFFAOYAV StdInChI Ref stdinchicite correct chemspider StdInChI 1S C6H6 c1 6 4 2 3 5 6 h2 5H,1H2 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey PGTKVMVZBBZCKQ UHFFFAOYSA N CASNo Ref cascite correct ?? CASNo 497 20 1 PubChem 136323 ChEBI Ref ebicite correct EBI ChEBI 51999 SMILES C C1 C C C C1 Section2 Chembox Properties Formula C sub 6 sub H sub 6 sub MolarMass 78.11 g mol Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Fulvene is one of several hydrocarbon s with the same formula as benzene , C sub 6 sub H sub 6 sub . Fulvenes include the derivatives of this simple hydrocarbon, which itself is rarely encountered. ref cite journal author Bergmann, E. D. title Fulvenes and Substituted Fulvenes journal Chemical Reviews volume 68 pages 41 84 year 1968 doi 10.1021 cr60251a002 ref Johannes Thiele chemist Thiele is credited with discovering the scope of the reaction between cyclopentadiene and aldehyde s and ketone s that yields the brightly coloured fulvene derivatives. ref cite journal author Thiele, J. title no umlaut Ueber Ketonreactionen bei dem Cyclopentadi n journal Chemische Berichte volume 33 pages 666 673 year 1900 doi 10.1002 cber.190003301113 ref Most fulvenes are prepared by the reactions starting from cyclopentadiene or sodium cyclopentadienyl. ref cite journal author Hafner, K. V pel, K. H. Ploss, G. K nig, C. title 6 Dimethylamino fulvene journal Organic Syntheses Coll. Vol. volume 5 pages 431 year 1973 url http www.orgsyn.org orgsyn pdfs CV5P0431.pdf ref 2,3,4,5 Tetramethylfulvene, abbreviated Me sub 4 sub Fv, is a relatively common ligand in orga ... more details
chembox ImageFile Cyclopentadienylthallium.svg ImageSize 100px IUPACName Thallium I cyclopentadienide OtherNames Thallium cyclopentadienide 5 Cyclopentadienyl thallium Section1 Chembox Identifiers ChemSpiderID 24721800 ChemSpiderID Ref chemspidercite correct chemspider InChI 1 C5H5.Tl c1 2 4 5 3 1 h1 5H q 1 1 InChIKey CVEQRUADOXXBRI UHFFFAOYAE StdInChI 1S C5H5.Tl c1 2 4 5 3 1 h1 5H q 1 1 StdInChIKey CVEQRUADOXXBRI UHFFFAOYSA N CASNo 34822 90 7 PubChem SMILES cH 1cccc1. Tl Section2 Chembox Properties C 5 H 5 Tl 1 Appearance Light yellow solid Density MeltingPtC 300 BoilingPt Solubility Insoluble Section3 Chembox Hazards EUClass Hazchem T RPhrases R26 28 , R33 , R36 37 38 SPhrases S13 , S28 , S45 NFPA H 3 NFPA F 0 NFPA R 0 Cyclopentadienylthallium , also known as thallium cyclopentadienide, is an Organothallium chemistry organothallium compound with formula C sub 5 sub H sub 5 sub Tl. This light yellow solid is insoluble in most organic solvents, but sublimes readily, and is useful as a precursor to transition metal and main group cyclopentadiene Cp compounds, as well as organic cyclopentadiene derivatives. ref Cite book author C. Elschenbroich, title Organometallics publisher Wiley VCH, Weinheim year 2006 page 130 isbn 3 527 29390 6 postscript None ref Preparation Cyclopentadienylthallium is prepared by the reaction of thallium I sulfate , sodium hydroxide , and cyclopentadiene ref cite journal title Cyclopentadienylthallium Thallium Cyclopentadienide author A.J. Nielson, C.E.F. Rickard, J.M. Smith journal Inorg. Synth. year 1986 volume 24 pages 97 99 doi 10.1002 9780470132555.ch31 ref Tl sub 2 sub SO sub 4 sub 2 NaOH 2 TlOH Na sub 2 sub SO sub 4 sub TlOH C sub 5 sub H sub 6 sub TlC sub 5 sub H sub 5 sub H sub 2 sub O Applications Compared to most of other cyclopentadienyl transfer reagent such as sodium cyclopentadienide cyclopentadienyl sodium , CpMgBr and Cp sub 2 sub Mg, cyclopentadienylthallium is less air sensitive. References reflist Category Metallocenes Cat ... more details
Chembox verifiedrevid 356377267 ImageFile Isoindene.png ImageSize 150px ImageName Skeletal formula ImageFile1 Isoindene 3D balls.png ImageName1 Ball and stick model IUPACName 2 H Indene OtherNames 2 H Isoindene Section1 Chembox Identifiers CASNo 270 53 1 PubChem SMILES C12 CCC C1C CC C2 Section2 Chembox Properties C 9 H 8 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Isoindene is a flammable polycyclic hydrocarbon with chemical formula C sub 9 sub H sub 8 sub . It is composed of a cyclohexadiene ring fused with a cyclopentadiene ring. See also Indene Isoindole Category Polycyclic nonaromatic hydrocarbons hydrocarbon stub ... more details
CPD can refer to any of the following US police departments Chicago Police Department Cincinnati Police Department Cleveland Police Department Columbus Police Department Certified Project Director as per IAPPM Town of Carmel Police Department , in New York Also Campaign for Peace and Democracy Cape Photographic Durchmusterung Centres of Plant Diversity Centre for Policy Dialogue Cephalo pelvic disproportion Cherry Poppin Daddies Chicago Park District Chronic pulmonary disease Collaborative Product Development Collaborative Professional Development Commission on Presidential Debates Committee on the Present Danger Concert of Parties for Democracy Conditional probability distribution Congress of People s Deputies AKA Congress of Soviets Contact potential difference Continuing Professional Development CPD gene , a human gene encoding the protein Carboxypeptidase D CPD Mark Critical Point Drying , a method of specimen preparation for electron microscopy Pyrimidine dimers Cyclobutane photodimers Cyclobutane Pyrimidine Dimer Cyclopentadiene CPD is the ICAO airline designator for Capital Airlines Limited Kenya PMD software Copy.2FPaste Detector .28CPD.29 PMD Copy&Paste Detector CPD disambig de CPD fr CPD it CPD ja CPD ru th CPD ... more details
CPH may refer to Concordia Publishing House the official publisher of The Lutheran Church Missouri Synod Chronic paroxysmal hemicrania CPH , a chronic headache caused by head injury. Close packed hexagonal is an arrangement of spheres into the closest packed arrangement. Communistische Partij Holland , a Dutch political party Copenhagen , the capital of Denmark CPH is the IATA airport code for Copenhagen Airport in Denmark . A Rail rollingstock in New South Wales Country Passenger Trains Rail Motor used in New South Wales , Australia . CPH is the ICAO airline designator for Champagne Airlines , France Critical Period Hypothesis in developmental biology , specifically regarding language acquisition, describes a theory of how there is a critical age at which a person can learn a language or speak a second language without an accent. Cyclopentadiene C sub 5 sub H sub 6 sub is sometimes abbreviated CpH, in line with the common use of Cp sup sup as an abbreviation for the cycpotentadienyl anion and of Cp in organometallic complexes ferrocene might be abbreviated as FeCp sub 2 sub or Cp sub 2 sub Fe, for example . disambig de CPH fr CPH it CPH nl CPH ja CPH ... more details
The Skatteb l rearrangement is an organic reaction for converting a geminal halogen dihalo cyclopropane to an allene using an organolithium base. ref Chemistry of gem Dihalocyclopropanes. V.1 Formation of Tricyclo 4.1.0.04,6 heptane and Derivatives Lars Skatteb l J. Org. Chem. 1966 31 9 2789 2794 DOI 10.1021 jo01347a014 . ref This rearrangement reaction is named after its discoverer, Lars Skatteb l , Professor emeritus at the University of Oslo . It proceeds through a carbene reaction intermediate File Skatteb l rearrangement general.png 500px center Skatteb l rearrangement When the cyclopropane ring is fitted with a 2 vinyl group, a cyclopentadiene is formed through a so called foiled carbene intermediate ref Chemistry of gem dihalocyclopropanes VI A novel synthesis of cyclopentadienes and fulvenes L. Skatteb l Tetrahedron journal Tetrahedron Volume 23, Issue 3 , 1967 , Pages 1107 1117 doi 10.1016 0040 4020 67 85060 9 . ref ref Leo A. Paquette and Mark L. McLaughlin Organic Syntheses , CV 8, 223 http www.orgsyn.org orgsyn orgsyn prepContent.asp?prep cv8p0223 Link . ref File Skatteb l rearrangement.png 500px center Skatteb l rearrangement References div class references small references div Category Rearrangement reactions Category Name reactions de Skatteb l Umlagerung zh Skatteb l ... more details
Chembox verifiedrevid 428743038 ImageFile Osmocene.svg ImageSize 100px ImageAlt IUPACName PIN OtherNames Section1 Chembox Identifiers CASNo 1273 81 0 CASNo Ref cascite correct ?? PubChem SMILES Section2 Chembox Properties C 10 H 10 Os 1 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Osmocene is an organoosmium compound found as a white solid. It is a metallocene . Osmocene is commercially available. It may be prepared by the reaction of osmium tetroxide with hydrobromic acid , followed by zinc and cyclopentadiene . ref cite journal last1 Bobyens first1 J. C. A. last2 Levendis first2 D. C. last3 Bruce first3 Michael I. last4 Williams first4 Michael L. title Crystal structure of osmocene, Os &eta C sub 5 sub H sub 5 sub sub 2 sub journal Journal of Crystallographic and Spectroscopic Research volume 16 pages 519 year 1986 doi 10.1007 BF01161040 issue 4 ref References references Osmium compounds Category Metallocenes Category Organoosmium compounds de Osmocen nl Osmoceen ... more details
Other uses Dimer disambiguation refimprove date April 2009 File Carboxylic acid dimers.png right thumb Dimers of carboxylic acid s are often found in vapour phase. A dimer is a chemical entity consisting of two structurally similar monomer s joined by bonds that can be either strong or weak. Organic chemistry File Dicyclopentadiene structure.svg thumb left 100px The dimer of cyclopentadiene although this might not be readily apparent on initial inspection Molecular dimers are often formed by the reaction of two identical compounds e.g. 2A A A. In this example, monomer A is said to dimerise to give the dimer A A . An example is Diaminocarbene s, which dimerise to give tetraaminoethylene s 2 C NR sub 2 sub sub 2 sub R sub 2 sub N sub 2 sub C C NR sub 2 sub sub 2 sub Acetic acid forms a dimer in the gas phase, the monomer units are held together by hydrogen bond s. Under special conditions, most OH containing molecules form dimers, e.g. the water dimer . Dicyclopentadiene is an unsymmetrical dimer of two cyclopentadiene molecules that have reacted in a Diels Alder reaction to give the product. Upon heating, it cracks undergoes a retro Diels Alder reaction to give identical monomers C sub 10 sub H sub 12 sub 2 C sub 5 sub H sub 6 sub The term homodimer is used when the two molecules are identical e.g. A A and heterodimer when they are not e.g. A B . The reverse of dimerisation is often called Dissociation chemistry dissociation . See also Monomer trimer chemistry Trimer Polymer Commonscat Dimers References cite web url http goldbook.iupac.org D01744.html title IUPAC Gold Book definition accessdate 2009 04 30 references http www.newton.dep.anl.gov askasci mole00 mole00420.htm Homo and hetero dimeric proteins Category Chemical compounds Category Oligomers Category Dimers ar ca D mer cs Dimer de Dimer et Dimeer es D mero qu mica fr Dim re fy Dimear ko id Dimer it Dimero he nl Dimeer ja oc Dim r pl Dimery pt D mero ru sr Dimer hemija fi Dime ... more details
Chembox verifiedrevid 444658035 Reference ref Merck Index , 11th Edition, 2744 ref ImageFile Di Cyclopentadiene ENDO & EXO V.2.svg ImageName Stereo wireframe model of dicyclopentadiene. ImageFile1 Dicyclopentadiene 3D balls.png ImageName1 Ball and stick model of dicyclopentadiene IUPACName Tricyclo 5.2.1.0 sup 2,6 sup deca 3,8 diene OtherNames 1,3 Dicyclopentadiene Section1 Chembox Identifiers Abbreviations DCPD StdInChI Ref stdinchicite correct chemspider StdInChI 1S C10H12 c1 2 9 7 4 5 8 6 7 10 9 3 1 h1 2,4 5,7 10H,3,6H2 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey HECLRDQVFMWTQS UHFFFAOYSA N CASNo 77 73 6 CASNo Ref cascite correct CAS PubChem 6492 PubChem Ref Pubchemcite PubChem1 6428576 PubChem1 Comment 6 R PubChem1 Ref Pubchemcite PubChem2 10396885 PubChem2 Comment 1 S ,7 R PubChem2 Ref Pubchemcite ChemSpiderID 6247 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID1 24532442 ChemSpiderID1 Comment sup 2 sup H sub 12 sub ChemSpiderID1 Ref Chemspidercite ChemSpiderID2 4933978 ChemSpiderID2 Comment 6 R ChemSpiderID2 Ref Chemspidercite ChemSpiderID3 8572323 ChemSpiderID3 Comment 1 S ,7 R ChemSpiderID3 Ref Chemspidercite EINECS 247 724 5 UNNumber UN 2048 KEGG Ref keggcite correct kegg KEGG C14411 MeSHName Dicyclopentadiene RTECS PC1050000 SMILES C1C CC2C1C3CC2C C3 InChI 1 C10H12 c1 2 9 7 4 5 8 6 7 10 9 3 1 h1 2,4 5,7 10H,3,6H2 InChIKey HECLRDQVFMWTQS UHFFFAOYAO Beilstein 1904092 Section2 Chembox Properties Formula C sub 10 sub H sub 12 sub MolarMass 132.20 g mol Density 0.98 g cm sup 3 sup MeltingPt 32.5 C BoilingPt 170 C Section7 Chembox Hazards FlashPt 32 C NFPA H 1 NFPA F 3 NFPA R 1 Dicyclopentadiene , abbreviated DCPD , is a chemical compound with formula C sub 10 sub H sub 12 sub . At room temperature, it is a white crystalline solid with a camphor ... undergoes a retro Diels Alder reaction to yield cyclopentadiene , a popular ligand in inorganic chemistry. The reaction is reversible and at room temperature cyclopentadiene slowly dimerizes ... more details
distinguish Tetrazene Image 1,2,3,4 tetrazine numbering.png thumb right 100px Structure of 1,2,3,4 tetrazine Image 1,2,4,5 tetrazine numbering.png thumb right 100px Structure of 1,2,4,5 tetrazine Tetrazine is an unstable Chemical compound compound that consists of a six membered aromatic ring containing four nitrogen atoms with the molecular formula Carbon C sub 2 sub Hydrogen H sub 2 sub Nitrogen N sub 4 sub . The name tetrazine is used in the IUPAC nomenclature nomenclature of derivatives of this compound. Three core ring isomer s exist 1,2,3,4 tetrazines , 1,2,3,5 tetrazines and 1,2,4,5 tetrazines . 1,2,3,4 tetrazines 1,2,3,4 Tetrazines are often isolated fused to an aromatic ring system and are stabilized as the dioxide derivatives. 1,2,4,5 tetrazine 1,2,4,5 Tetrazines are very well known and myriad 3,6 disubstituted 1,2,4,5 tetrazines are known. ref see United States Patent 6645325 ref These materials are of use in the area of energetic chemistry. The compound 3,6 di 2 pyridyl 1,2,4,5 tetrazine ref Datasheet http www.sigmaaldrich.com catalog search ProductDetail ALDRICH 403547 Link ref has two pyridine substituents and is of importance as a reagent in Diels Alder reaction s. It reacts with norbornadiene in a sequence of one DA reactions and two retro DA reactions to cyclopentadiene and a pyridazine with exchange of an acetylene unit Image DielsAlderCycloadditionDTP.png 500px reaction of norbornadiene with 3,6 di 2 pyridyl 1,2,4,5 tetrazine With norbornadiene fused to an arene the reaction stops at an intermediary stage ref 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 . Ronald N. Warrener and Peter A. Harrison Molecules journal Molecules 2001 , 6, 353 369 http www.mdpi.org molecules papers 60400353.pdf Online Article ref See also 6 membered rings with one nitrogen atom pyridine s 6 membered rings with two nitrogen atoms ... more details
. Ionic type complexes are generally synthesized directly by reaction of cyclopentadiene ... robust complexes, cyclopentadiene is employed in the presence of a conventional base chemistry base such as NaOH. Specialized alternatives to NaCp include trimethylsilyl cyclopentadiene Cp ... sup , or Cp sup nowiki &minus nowiki sup , to metals. Relative to the more common cyclopentadiene ... more details
The Aza Diels Alder reaction converts imine s and diene s to tetrahydropyridine s. This organic reaction is a modification of the Diels Alder reaction . The nitrogen atom can be part of the diene or the dienophile . Image Aza Diels Alder.gif center The Aza Diels Alder reaction, general scope The imine is often generated in situ from an amine and formaldehyde . An example is the reaction of cyclopentadiene with benzylamine to an aza norbornene . ref N benzyl 2 azanorbornene Paul A. Grieco and Scott D. Larsen Organic Syntheses , Coll. Vol. 8, p.31 Vol. 68, p.206 http www.orgsyn.org orgsyn prep.asp?prep cv8p0031 Article ref Image Aza Diels Alder phenylmethylamine.gif center In the enantioselective Diels Alder DA reaction of an aniline , formaldehyde and a cyclohexenone catalysis catalyzed by S proline even the diene is masked. ref Direct Catalytic Enantioselective Aza Diels Alder Reactions Henrik Sund n, Ismail Ibrahem, Lars Eriksson, Armando C rdova Angewandte Chemie International Edition 4877 2005 http www3.interscience.wiley.com cgi bin abstract 110546882 ABSTRACT Abstract ref Image Aza Diels Alder proline.gif center S proline enantioselective Aza Diels Alder reaction The catalytic cycle starts with the reactions of the aromatic amine with formaldehyde to the imine and the reaction of the ketone with proline to the diene. The second step, an endo trig cyclisation , is driven to one of the two possible enantiomer s 99 enantiomeric excess ee because the imine nitrogen atom forms a hydrogen bond with the carboxylic acid group of proline on the Si face . Hydrolysis of the final complex releases the product and regenerates the catalyst. Image Aza DA mechanism.gif center catalytic cycle for S proline enantioselective Aza Diels Alder reaction See also Oxo Diels Alder reaction References references Category Cycloadditions Category Heterocycle forming reactions Category Name reactions nl Aza Diels Alder reactie ... more details
Chembox verifiedrevid 401973876 Name Cyclopentene ImageFileL1 Cyclopentene 2D skeletal.png ImageSizeL1 100px ImageNameL1 Cyclopentene ImageFileR1 Cyclopentene 3D balls.png ImageSizeR1 100px ImageNameR1 Ball and stick model of cyclopentene ImageFile2 Cyclopentene 3D vdW.png ImageSize2 120px ImageName2 Space filling model of cyclopentene IUPACName Cyclopentene Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 8544 PubChem 8882 InChI 1 C5H8 c1 2 4 5 3 1 h1 2H,3 5H2 InChIKey LPIQUOYDBNQMRZ UHFFFAOYAS StdInChI Ref stdinchicite correct chemspider StdInChI 1S C5H8 c1 2 4 5 3 1 h1 2H,3 5H2 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey LPIQUOYDBNQMRZ UHFFFAOYSA N CASNo Ref cascite correct CAS CASNo 142 29 0 ChEBI 49155 SMILES C1CC CC1 Section2 Chembox Properties Formula C sub 5 sub H sub 8 sub MolarMass 68.11 g mol Density 0.744 g cm sup 3 sup MeltingPt 135 C BoilingPt 44 C Section7 Chembox Hazards FlashPt 29 C NFPA H 1 NFPA F 3 NFPA R 1 NFPA R Section8 Chembox Related OtherCpds Cyclopentadiene br Cyclobutene Cyclopentene is a chemical compound with the formula Carbon sub 5 sub Hydrogen sub 8 sub . It is a colorless liquid with a petrol like odor . It is one of the cycloalkene s. Cyclopentene is produced industrially in large amounts. It is used as a monomer for synthesis of plastic s, and in a number of chemical syntheses. It can be obtained from vinylcyclopropane in the vinylcyclopropane cyclopentene rearrangement . References Unreferenced date September 2007 Reflist Cycloalkenes Hydrocarbon stub Category Cycloalkenes Category Monomers ar de Cyclopenten fr Cyclopent ne it Ciclopentene hu Ciklopent n nl Cyclopenteen ja pt Ciclopenteno sr Ciklopenten vi Cyclopenten zh ... more details
Chembox SystematicName Cyclopenta 2,4 dien 1 yl ref name cyclopentadienyl CHEBI 36769 Cite web url https www.ebi.ac.uk chebi searchId.do?chebiId 36769 title cyclopentadienyl CHEBI 36769 work Chemical Entities of Biological interest ChEBI location UK publisher European Bioinformatics Instititute ref OtherNames Cyclopentadienyl radical ref name cyclopentadienyl CHEBI 36769 ImageFile Cyclopentadienyl Anion.svg ImageCaption Cyclopentadienyl anion ImageSize 100px Section1 Chembox Identifiers CASNo 2143 53 5 PubChem 137443 PubChem Ref Pubchemcite correct pubchem ChemSpiderID 121110 ChemSpiderID Ref chemspidercite correct chemspider ChEBI 36769 Beilstein 2070324 Gmelin 323080 SMILES c1cccc1 SMILES1 CH 1C CC C1 StdInChI 1S C5H5 c1 2 4 5 3 1 h1 5H StdInChI Ref stdinchicite correct chemspider StdInChIKey HPYIUKIBUJFXII UHFFFAOYSA N StdInChIKey Ref stdinchicite correct chemspider Section2 Chembox Properties C 5 H 5 ExactMass 65.039125160 g mol sup 1 sup In organic chemistry , cyclopentadienyl is a cyclic compound cyclic group of atoms with the formula carbon C sub 5 sub hydrogen H sub 5 sub . Cyclopentadienyl are closely related to cyclopentadiene . Cyclopentadienyl have five carbon atoms bonded together in a pentagonal planar ring, all five of which are bonded to individual hydrogen atoms. Cyclopentadienyl is aromaticity chemically aromatic and show equal bond lengths between carbon atoms in the ring. Cyclopentadienyl is known in organometallic chemistry where it forms cyclopentadienyl complex es. References Reflist Category Organic chemistry es Ciclopentadienilo nl Cyclopentadienyl ... more details
and cyclopentadiene is allowed by the Woodward Hoffmann rules because there are six electrons ... between maleic anhydride and cyclopentadiene, the Endo exo isomerism endo product is favored ..., only the reaction between the HOMO of cyclopentadiene and the LUMO of maleic anhydride is allowed. Furthermore ... product forms faster it is the major product. ref name fleming File Cyclopentadiene Maleic Anhydride ... more details
chembox verifiedrevid 407630535 ImageFile Benzvalene.svg ImageSize IUPACName tricyclo 3.1.0.0 sup 2,6 sup hex 3 ene OtherNames Section1 Chembox Identifiers CAS CAS 6 5 9 8 5 8 PubChem 136470 chEBI SMILES C1 CC2C3C1C23 InChI 1 C6H6 c1 2 4 5 3 1 6 4 5 h1 6H Section2 Chembox Properties Formula C sub 6 sub H sub 6 sub MolarMass 78.1 g mol Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Benzvalene is an organic compound and one of several isomer s of benzene . ref cite DOI 10.1002 anie.198105291 ref . It was synthesised in 1971 by Thomas J. Katz et al. ref cite DOI 10.1021 ja00744a045 ref ref cite DOI 10.1021 jo990883g ref The 1971 synthesis consisted of treating cyclopentadiene with methyllithium in dimethylether and then with dichloromethane and methyllithium in at 45 C. The hydrocarbon in solution was described as having an extraordinary foul odor. Due to the high steric strain present in benzvalene, the pure compound easily detonates, for example by scratching. The compound converts to benzene with a chemical half life of approximately 10 days. This symmetry forbidden transition is believed to take place through a diradical intermediate ref Rearrangements and interconversions of compounds of the formula CH n Lawrence T. Scott, Maitland. Jones Chem. Rev. , 1972, 72 2 , pp 181 202 DOI 10.1021 cr60276a004 ref Polybenzvalene Benzvalene can be polymerized in a Ring opening metathesis polymerisation ROMP process to polybenzvalene ref cite DOI 10.1021 ja00217a049 ref . This polymer contains highly strained bicyclobutane rings which again makes it a sensitive material. The rings can be isomerization isomerized to 1,3 dienes and for this reason polybenzvalene has been investigated as a precursor to polyacetylene . References Reflist Category Alkenes de Benzvalen fr Benzval ne it Benzvalene nl Benzvaleen zh ... more details
Orphan date February 2011 The telomerization is the linear Dimer chemistry dimerization of 1,3 dienes with simultaneous addition of a nucleophile in a catalytic reaction. Reaction The reaction was independently discovered by E. J. Smutny at Shell Oil Company Shell and Takahashi at the Osaka University in the late sixties. The general reaction equation is as follows File Telomerisation.png center 400px thumb Products of the Telomerisation of 1,3 Butadiene The formation of several isomers are possible. In addition to 1,3 butadiene also substituted dienes such as isoprene or cyclic dienes such as cyclopentadiene can be used. A variety of substances such as water , ammonia , alcohol s, or C H acidic compounds can be used as nucleophile s. When water is used, for example di unsaturated alcohols are obtained. The catalysts used are mainly metal organic palladium and nickel compounds. In 1991, Kuraray implemented the production of 1 octanol on an industrial scale 5000 t a 1 . The commercial route to produce 1 octene based on butadiene as developed by Dow Chemical came on stream in Tarragona in 2008. The telomerization of butadiene with methanol in the presence of a palladium catalyst yields 1 methoxy 2,7 octadiene, which is fully hydrogenated to 1 methoxyoctane in the next step. Subsequent cracking of 1 methoxyoctane gives 1 octene and methanol for recycle. External links A. Behr http books.google.de books?id phZcSma9ps0C&pg PA418&lpg PA418&dq smutny shell telomerisation&source web&ots s0H WtkA7L&sig qOjqLKL8sMMBRJc2r8y6qtL C0I&hl de&sa X&oi book result&resnum 4&ct result Angewandte homogene Katalyse as Google Book in German Literature P. Fischer process concepts for the transition telomerization of isoprene with water or methanol. Shaker Verlag, 2002, 176 pages, ISBN 3832204148, ISBN 978 3832204143 EJ Smutny, J. Amer. Chem. 89 1967 6793 S. Takahashi, Tetrahedron Lett. 1967, 2451 A. Behr, M. Becker, T. Beckmann, L. Johnen, J. Leschinski, S. Reyer, Angew. Chem. Int. Ed. 200 ... more details
chembox verifiedrevid 417625501 Name CpRuCl PPh sub 3 sub sub 2 sub ImageFile1 Chloro cyclopentadienyl bis triphenylphosphine ruthenium.png ImageSize1 120px ImageFile2 Chloro cyclopentadienyl bis triphenylphosphine ruthenium from xtal 1992 3D balls.png ImageSize2 220px Section1 Chembox Identifiers CASNo Ref CASNo 32993 05 8 Section2 Chembox Properties Formula C sub 41 sub H sub 35 sub ClP sub 2 sub Ru MolarMass 726.19 g mol Appearance Orange solid Solubility Insoluble MeltingPt 135 C 408 K RPhrases R20 21 22 R36 37 38 SPhrases S22 S26 S36 37 39 Chloro cyclopentadienyl bis triphenylphosphine ruthenium is the organoruthenium half sandwich compound with formula RuCl PPh sub 3 sub sub 2 sub C sub 5 sub H sub 5 sub . It as an air stable orange crystalline solid that is used in a variety of organometallic synthetic and catalytic transformations. Structure and Properties The compound has idealized C sub s sub symmetry. It is soluble in chloroform, dichloromethane, and acetone. Preparation Chloro cyclopentadienyl bis triphenylphosphine ruthenium was first reported in 1969 when it was prepared by reacting dichlorotris triphenylphosphine ruthenium II with cyclopentadiene. ref cite journal author Gilbert, J. Wilkinson, G. title New Complexes of Ruthenium II with Triphenylphosphine and other Ligands journal J. Chem. Soc. doi 10.1039 J19690001749 year 1969 pages 1749 ref RuCl sub 2 sub PPh sub 3 sub sub 3 sub C sub 5 sub H sub 6 sub RuCl PPh sub 3 sub sub 3 sub C sub 5 sub H sub 5 sub HCl It is easily prepared from ruthenium III chloride , triphenylphosphine , and cyclopentadiene in ethanol. ref Bruce, M., Hamiester, C., Swincer, A., Wallis, R., and Ittel, S. 1982 . Some Cyclopentadienylruthenium II Complexes Containing Triphenylphosphine. Inorganic Syntheses 1982 . 78 82. DOI 10.1002 9780470132524 ref Reactions Chloro cyclopentadienyl bis triphenylphosphine ruthenium II undergoes a variety of substitution reactions often by involving substitution of the chloride. With phenylace ... more details
Image Lactams General Formulae V.1.png thumb right 450px From left to right, general structures of a lactam, a lactam, a lactam and a lactam. A lactam the noun is a portmanteau of the words lactone amide is a Cyclic compound cyclic amide . Prefixes indicate how many carbon atoms apart from the carbonyl moiety are present in the ring beta lactam lactam 2 carbon atoms outside the carbonyl, 4 ring atoms in total , lactam 3 and 5 , lactam 4 and 6 . Beta letter Beta , gamma and Delta letter delta are the second, third and fourth letters in the alphabetical order of the Greek alphabet , respectively. Synthesis This section is linked from Organic reaction General synthetic methods exist for the organic synthesis of lactams. Lactams form by the acid catalyzed rearrangement of oximes in the Beckmann rearrangement . Lactams form from cyclic ketones and hydrazoic acid in the Schmidt reaction . Lactams form from cyclisation of amino acids . In iodolactamization ref Spencer Knapp, Frank S. Gibson Organic Syntheses , Coll. Vol. 9, p.516 1998 Vol. 70, p.101 1992 http orgsynth.org orgsyn prep.asp?prep cv9p0516 Online article ref an iminium ion reacts with an halonium ion formed in situ by reaction of an alkene with iodine . Image Iodolactamization.png 700px Iodolactamization reaction Lactams form by copper catalyzed 1,3 dipolar cycloaddition of alkynes and nitrones in the Kinugasa reaction Diels Alder reaction between cyclopentadiene and chlorosulfonyl isocyanate CSI can be utilized to obtain both as well as lactam. At lower temp 78 C lactam is the preferred product. At optimum temperatures, a highly useful lactam known as Vince Lactam is obtained. ref Pham, P. T. Vince, R. Phosphorus, Sulphur and Silicon 2007 , 779 791. ref File Preparation of VL and beta lactam.JPG Preparation of VL and beta lactam Tautomerization to Lactim Lactim is a cyclic carboximidic acid compound characterized by an endocyclic carbon nitrogen double bond . It is formed when l ... more details
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