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Fulvenes

February 12, 2024

Fulvenes are the class of hydrocarbon obtained by formally cross-conjugating one ring and methylidene through a common exocyclic double bond.[1][2]

Chemical structure of fulvene

The name is derived from fulvene, which has one pentagonal ring. Other examples include methylenecyclopropene (triafulvene) and heptafulvene.

Subclasses edit

Several types of fulvenes are defined.[3] They are:

Preparation edit

Fulvenes are readily prepared by the condensation of cyclopentadiene and aldehydes and ketones:

C5H6 + R2C=O → C4H4C=CR2 + H2O

Thiele is credited with discovering this reaction.[4][5]

Modern synthesis of fulvenes employ buffer systems.[6][7]

Ligand in organometallic chemistry edit

Fulvenes are common ligands and ligand precursors in organometallic chemistry.[8] 2,3,4,5-Tetramethylfulvene, abbreviated Me4Fv, results from the deprotonation of cationic pentamethylcyclopentadienyl complexes.[9] Some Me4Fv complexes are called tuck-in complexes.

 
η4- and η6-fulvene complexes

References edit

  1. ^ Agranat, Israel (2012), "Ground-State Versus Excited-State Polarity of Triafulvenes: A Study of Solvent Effects on Molecular Electronic Spectra", The Jerusalem Symposia on Quantum Chemistry and Biochemistry, 8: 573–583, doi:10.1007/978-94-010-1837-1_36
  2. ^ Neuenschwander, Markus (1986), "Synthetic and NMR spectroscopic investigations of fulvenes and fulvalenes" (PDF), Pure Appl. Chem., 58 (1): 55–66, doi:10.1351/pac198658010055
  3. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "Fulvenes". doi:10.1351/goldbook.F02550
  4. ^ Thiele, J. (1900). "Ueber Ketonreactionen bei dem Cyclopentadiën". Chemische Berichte. 33: 666–673. doi:10.1002/cber.190003301113.
  5. ^ Hafner, K.; Vöpel, K. H.; Ploss, G.; König, C. (1967). "6-(Dimethylamino)Fulvene". Organic Syntheses. 47: 52. doi:10.15227/orgsyn.047.0052.
  6. ^ Coşkun, Necdet; Erden, Ihsan (2011-11-11). "An efficient catalytic method for fulvene synthesis". Tetrahedron. 67 (45): 8607–8614. doi:10.1016/j.tet.2011.09.036. ISSN 0040-4020. PMC 3196336. PMID 22021940.
  7. ^ Sieverding, Paul; Osterbrink, Johanna; Besson, Claire; Kögerler, Paul (2019-01-18). "Kinetics and mechanism of pyrrolidine buffer-catalyzed fulvene formation". J. Org. Chem. 84 (2): 486–494. doi:10.1021/acs.joc.8b01660. ISSN 0022-3263. PMID 30540466.
  8. ^ Strohfeldt, Katja; Tacke, Matthias (2008). "Bioorganometallic fulvene-derived titanocene anti-cancer drugs". Chemical Society Reviews. 37 (6): 1174–87. doi:10.1039/B707310K. PMID 18497930.
  9. ^ Kreindlin, A. Z.; Rybinskaya, M. A. (2004). "Cationic and Neutral Transition Metal Complexes with a Tetramethylfulvene or Trimethylallyldiene Ligand". Russian Chemical Reviews. 73 (5): 417–432. Bibcode:2004RuCRv..73..417K. doi:10.1070/RC2004v073n05ABEH000842.

February 12, 2024
fulvenes, class, hydrocarbon, obtained, formally, cross, conjugating, ring, methylidene, through, common, exocyclic, double, bond, chemical, structure, fulvenethe, name, derived, from, fulvene, which, pentagonal, ring, other, examples, include, methylenecyclop. Fulvenes are the class of hydrocarbon obtained by formally cross conjugating one ring and methylidene through a common exocyclic double bond 1 2 Chemical structure of fulveneThe name is derived from fulvene which has one pentagonal ring Other examples include methylenecyclopropene triafulvene and heptafulvene Contents 1 Subclasses 2 Preparation 3 Ligand in organometallic chemistry 4 ReferencesSubclasses editSeveral types of fulvenes are defined 3 They are triafulvene pentafulvene heptafulvene nonafulvenePreparation editFulvenes are readily prepared by the condensation of cyclopentadiene and aldehydes and ketones C5H6 R2C O C4H4C CR2 H2OThiele is credited with discovering this reaction 4 5 Modern synthesis of fulvenes employ buffer systems 6 7 Ligand in organometallic chemistry editFulvenes are common ligands and ligand precursors in organometallic chemistry 8 2 3 4 5 Tetramethylfulvene abbreviated Me4Fv results from the deprotonation of cationic pentamethylcyclopentadienyl complexes 9 Some Me4Fv complexes are called tuck in complexes nbsp h4 and h6 fulvene complexesReferences edit Agranat Israel 2012 Ground State Versus Excited State Polarity of Triafulvenes A Study of Solvent Effects on Molecular Electronic Spectra The Jerusalem Symposia on Quantum Chemistry and Biochemistry 8 573 583 doi 10 1007 978 94 010 1837 1 36 Neuenschwander Markus 1986 Synthetic and NMR spectroscopic investigations of fulvenes and fulvalenes PDF Pure Appl Chem 58 1 55 66 doi 10 1351 pac198658010055 IUPAC Compendium of Chemical Terminology 2nd ed the Gold Book 1997 Online corrected version 2006 Fulvenes doi 10 1351 goldbook F02550 Thiele J 1900 Ueber Ketonreactionen bei dem Cyclopentadien Chemische Berichte 33 666 673 doi 10 1002 cber 190003301113 Hafner K Vopel K H Ploss G Konig C 1967 6 Dimethylamino Fulvene Organic Syntheses 47 52 doi 10 15227 orgsyn 047 0052 Coskun Necdet Erden Ihsan 2011 11 11 An efficient catalytic method for fulvene synthesis Tetrahedron 67 45 8607 8614 doi 10 1016 j tet 2011 09 036 ISSN 0040 4020 PMC 3196336 PMID 22021940 Sieverding Paul Osterbrink Johanna Besson Claire Kogerler Paul 2019 01 18 Kinetics and mechanism of pyrrolidine buffer catalyzed fulvene formation J Org Chem 84 2 486 494 doi 10 1021 acs joc 8b01660 ISSN 0022 3263 PMID 30540466 Strohfeldt Katja Tacke Matthias 2008 Bioorganometallic fulvene derived titanocene anti cancer drugs Chemical Society Reviews 37 6 1174 87 doi 10 1039 B707310K PMID 18497930 Kreindlin A Z Rybinskaya M A 2004 Cationic and Neutral Transition Metal Complexes with a Tetramethylfulvene or Trimethylallyldiene Ligand Russian Chemical Reviews 73 5 417 432 Bibcode 2004RuCRv 73 417K doi 10 1070 RC2004v073n05ABEH000842 Retrieved from https en wikipedia org w index php title Fulvenes amp oldid 1163900162, wikipedia, wiki, book, books, library,

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