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Fulvene information


Fulvene
Names
Preferred IUPAC name
5-Methylidenecyclopenta-1,3-diene[1]
Other names
Fulvene[1]
5-Methylene-1,3-cyclopentadiene
Identifiers
CAS Number
  • 497-20-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:51999 checkY
ChemSpider
  • 120097 checkY
PubChem CID
  • 136323
UNII
  • 19W699IKIE checkY
CompTox Dashboard (EPA)
  • DTXSID30897602 Edit this at Wikidata
InChI
  • InChI=1S/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2 checkY
    Key: PGTKVMVZBBZCKQ-UHFFFAOYSA-N checkY
  • InChI=1/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2
    Key: PGTKVMVZBBZCKQ-UHFFFAOYAV
SMILES
  • C=C1\C=C/C=C1
Properties
Chemical formula
C6H6
Molar mass 78.114 g·mol−1
Magnetic susceptibility (χ)
-42.9·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Fulvene (pentafulvene) is a hydrocarbon with the formula (CH=CH)2C=CH2. It is a prototype of a cross-conjugated hydrocarbon.[2] Fulvene is rarely encountered,[3] but substituted derivatives (fulvenes) are numerous. They are mainly of interest as ligands and precursors to ligands in organometallic chemistry.

Fulvene is an isomer of benzene, which when irradiated at 237 to 254 nm forms small amounts of fulvene along with benzvalene.[4]

  1. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 379. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Preethanuj Preethalayam; Syam krishnan, K.; Sreeja Thulasi; Sarath Chand,S.; Jomy Joseph; Vijay Nair; Florian Jaroschik; K.V.Radhakrishnan (2017). "Recent Advances in the Chemistry of Pentafulvenes". Chemical Reviews. 117 (5): 3930–3989. doi:10.1021/acs.chemrev.6b00210. PMID 28151643.
  3. ^ Bergmann, E. D. (1968). "Fulvenes and Substituted Fulvenes". Chemical Reviews. 68: 41–84. doi:10.1021/cr60251a002.
  4. ^ Kaplan, Louis; Wilzbach, K. E. (1968). "Photolysis of benzene vapor. Benzvalene formation at wavelengths 2537-2370 A". Journal of the American Chemical Society. 90 (12): 3291–3292. doi:10.1021/ja01014a086. ISSN 0002-7863.

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Fulvene

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Fulvene (pentafulvene) is a hydrocarbon with the formula (CH=CH)2C=CH2. It is a prototype of a cross-conjugated hydrocarbon. Fulvene is rarely encountered...

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Fulvenes

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Fulvenes are the class of hydrocarbon obtained by formally cross-conjugating one ring and methylidene through a common exocyclic double bond. The name...

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C6H6

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Benzene Benzvalene Bicyclopropenyl 1,2,3-Cyclohexatriene Dewar benzene Fulvene Prismane [3]Radialene 3-Methylidenepent-1-en-4-yne Hexadiyne 1,3-Hexadiyne...

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Methylenecyclopropene

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exocyclic double bond attached. Methylenecyclopropene is the smallest of the fulvenes (a family of unstable, cyclic molecules, conjugated transversally with...

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Benzvalene

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diethyl ether at −45 °C. It can also be formed in low yield (along with fulvene and Dewar benzene) by irradiation of benzene at 237 to 254 nm. The hydrocarbon...

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Annulene

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([22]-annulene) Wikimedia Commons has media related to Annulenes. Annulyne Circulene Fulvenes IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997)...

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Thermodynamic versus kinetic reaction control

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They were re-investigating a reaction between maleic anhydride and a fulvene first reported in 1929 by Otto Diels and Kurt Alder. They observed that...

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Mycena leaiana

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Anke T, Scherer A, Steglich W. (1990). "Leaianafulvene, a sesquiterpenoid fulvene derivative from cultures of Mycena leaiana". Phytochemistry 12: 3942–3944...

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List of compounds with carbon number 6

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phenylthio radical 4985-62-0 C6H6 benzene 71-43-2 C6H6 benzvalene 659-85-8 C6H6 fulvene 497-20-1 C6H6Cl2Si phenyldichlorosilane 1631-84-1 C6H6Cl6 lindane 58-89-9...

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Alkyne trimerisation

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macrocylic and acyclic triynes with Group 6 metal carbonyls. The formation of fulvene and benzene". J. Am. Chem. Soc. 106 (26): 8315. doi:10.1021/ja00338a063...

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Fulvalenes

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exocyclic double bond. The name is derived from the similarly structured fulvenes which lack one ring. Pentafulvalene (2) is also called simply fulvalene...

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Triafulvalene

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Neuenschwander, Markus (1986), "Synthetic and NMR spectroscopic investigations of fulvenes and fulvalenes" (PDF), Pure Appl. Chem., 58 (1): 55–66, doi:10.1351/pac198658010055...

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Sesquifulvalene

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the π-Electronic Structure of Singlet, Triplet, and Quintet States of Fulvenes and Fulvalenes Using the Electron Localization Function". The Journal of...

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Fulvalene

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Perchlorofulvalene (C4Cl4C)2 is quite stable in contrast to fulvalene itself. Fulvenes, (CH=CH)2C=CH2 and substituted derivatives Tetrathiafulvalene, C2H2S2C=CS2C2H2...

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Ketene cycloaddition

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dienes, the larger ketene substituent is placed in the endo position. Fulvenes typically react in the ring, leaving the double bond intact. (6) Ketenes...

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Titanocene Y

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Particularly, lipophilic titanocene dichloride derivatives derived from fulvenes were synthesised in structural diversity and this led to the development...

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