Fulvene: Difference between revisions

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	{{chembox		{{chembox
			\| Watchedfields = changed
	\| verifiedrevid = ~~443828084~~		\| verifiedrevid = 443829334
⚫	\|ImageFileL1=Fulvene.~~png~~
			\| Name =
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			\| ImageFile =
⚫	\|ImageFileR1=Fulvene_3D.png
		⚫	\| ImageFileL1 = Fulvene with hydrogens.svg
⚫	\|ImageSizeR1=120px
		⚫	\| ImageSizeL1 = 120px
⚫	\|IUPACName=~~Fulvene~~
		⚫	\| ImageFileR1 = Fulvene_3D.png
⚫	\|OtherNames=5-Methylene-1,3-cyclopentadiene
		⚫	\| ImageSizeR1 = 120px
⚫	\|Section1={{Chembox Identifiers
			\| PIN = 5-Methylidenecyclopenta-1,3-diene<ref name=iupac2013>{{cite book \| title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) \| publisher = ] \| date = 2014 \| location = Cambridge \| page = 379 \| doi = 10.1039/9781849733069-FP001 \| isbn = 978-0-85404-182-4}}</ref>
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\| SystematicName =
		⚫	\| OtherNames = Fulvene<ref name=iupac2013 /><br />5-Methylene-1,3-cyclopentadiene
		⚫	\| IUPACName =
		⚫	\| Section1 = {{Chembox Identifiers
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 120097		\| ChemSpiderID = 120097
	\| InChI = 1/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2		\| InChI = 1/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2
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	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = PGTKVMVZBBZCKQ-UHFFFAOYSA-N		\| StdInChIKey = PGTKVMVZBBZCKQ-UHFFFAOYSA-N
		⚫	\| CASNo_Ref = {{cascite\|correct\|??}}
	\| CASNo=497-20-1		\| CASNo=497-20-1
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
⚫	\| PubChem=136323
			\| UNII = 19W699IKIE
⚫	\| ~~ChEBI_Ref~~ = {{~~ebicite~~\|correct\|~~EBI~~}}
		⚫	\| PubChem=136323
			\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 51999		\| ChEBI = 51999
	\| SMILES = C=C1\C=C/C=C1		\| SMILES = C=C1\C=C/C=C1
	}}		}}
	\|Section2={{Chembox Properties		\| Section2 = {{Chembox Properties
			\| C=6\|H=6
	\| Formula=C<sub>6</sub>H<sub>6</sub>
			\| Appearance=
	\| MolarMass=78.11 g/mol
	\| ~~Appearance~~=		\| Density=
	\| ~~Density~~=		\| MeltingPt=
	\| ~~MeltingPt~~=		\| BoilingPt=
	\| ~~BoilingPt~~=		\| Solubility=
			\| MagSus = -42.9·10<sup>−6</sup> cm<sup>3</sup>/mol
	\| Solubility=
	}}		}}
	\|Section3={{Chembox Hazards		\| Section3 = {{Chembox Hazards
	\| MainHazards=		\| MainHazards=
	\| FlashPt=		\| FlashPt=
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	\| Autoignition=
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			\| Section4 =
			\| Section5 =
			\| Section6 =
	}}		}}
			'''Fulvene''' (pentafulvene) is a ] with the formula (CH=CH)<sub>2</sub>C=CH<sub>2</sub>. It is a prototype of a ] hydrocarbon.<ref>{{cite journal\|author1=Preethanuj Preethalayam \|author2=Syam krishnan, K.\|author3=Sreeja Thulasi \|author4= Sarath Chand, S. \|author5=Jomy Joseph

			\|author6= Vijay Nair
	'''Fulvene''' is one of several ]s with the same formula as ], C<sub>6</sub>H<sub>6</sub>. Fulvenes include the derivatives of this simple hydrocarbon, which itself is rarely encountered.<ref>{{cite journal
			\|author7=Florian Jaroschik\|author8=K.V.Radhakrishnan
			\|title= Recent Advances in the Chemistry of Pentafulvenes.
		⚫	\|journal = Chemical Reviews
			\|year=2017\|volume= 117\|issue=5\|pages= 3930–3989
			\|doi=10.1021/acs.chemrev.6b00210\|pmid=28151643}}</ref> Fulvene is rarely encountered,<ref>{{cite journal
	\| author = Bergmann, E. D.		\| author = Bergmann, E. D.
	\| title = Fulvenes and Substituted Fulvenes		\| title = Fulvenes and Substituted Fulvenes
Line 45:		Line 61:
	\| pages = 41–84		\| pages = 41–84
	\| year = 1968		\| year = 1968
	\| doi = 10.1021/cr60251a002}}</ref> ~~] is ~~credited~~ ~~with~~ ~~discovering~~ ~~the~~ ~~scope~~ of ~~the~~ ~~reaction between~~ ] and ]s ~~and~~ ]~~s that affords the brightly coloured fulvene derivatives~~.~~<ref>{{cite journal~~~~		\| doi = 10.1021/cr60251a002}}</ref> but substituted derivatives (]) are numerous. They are mainly of interest as ]s and precursors to ligands in ].

	\| author = Thiele, J.
			Fulvene is an isomer of ], which when irradiated at 237 to 254 nm forms small amounts of fulvene along with ].<ref>{{Cite journal \|last=Kaplan \|first=Louis \|last2=Wilzbach \|first2=K. E. \|date=1968 \|title=Photolysis of benzene vapor. Benzvalene formation at wavelengths 2537-2370 A \|url=https://pubs.acs.org/doi/abs/10.1021/ja01014a086 \|journal=Journal of the American Chemical Society \|language=en \|volume=90 \|issue=12 \|pages=3291–3292 \|doi=10.1021/ja01014a086 \|issn=0002-7863}}</ref>
	\| title = <!--no umlaut-->Ueber Ketonreactionen bei dem Cyclopentadiën
	\| journal = ]
	\| 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.; Vöpel, K. H.; Ploss, G.; König, 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>

			== See also ==
	2,3,4,5-Tetramethylfulvene, abbreviated Me<sub>4</sub>Fv, is a relatively common ligand in ]. It typically results from the deprotonation of cationic ] complexes.<ref>{{cite journal
			*]
	\| author = Kreindlin, A. Z.; Rybinskaya, M. A.
			*]
	\| title = Cationic and Neutral Transition Metal Complexes with a Tetramethylfulvene or Trimethylallyldiene Ligand
⚫	\| journal = ~~Russian~~ Chemical Reviews
	\| volume = 73
	\| pages = 417–432
	\| year = 2004
	\| doi = 10.1070/RC2004v073n05ABEH000842}}</ref>

	==References==		==References==
	{{reflist}}		{{reflist}}

			{{Authority control}}
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Latest revision as of 22:12, 3 September 2024

Fulvene

Names

Preferred IUPAC name 5-Methylidenecyclopenta-1,3-diene

Other names Fulvene
5-Methylene-1,3-cyclopentadiene

Identifiers

CAS Number

497-20-1

3D model (JSmol)

Interactive image

ChEBI

CHEBI:51999

ChemSpider

120097

PubChem CID

136323

UNII

19W699IKIE

CompTox Dashboard (EPA)

DTXSID30897602

InChI

InChI=1S/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2Key: PGTKVMVZBBZCKQ-UHFFFAOYSA-N
InChI=1/C6H6/c1-6-4-2-3-5-6/h2-5H,1H2Key: PGTKVMVZBBZCKQ-UHFFFAOYAV

SMILES

C=C1\C=C/C=C1

Properties

Chemical formula

C₆H₆

Molar mass

78.114 g·mol

Magnetic susceptibility (χ)

-42.9·10 cm/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).

Y verify (what is ?) Infobox references

Chemical compound

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, 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.

References

^ 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.
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.
Bergmann, E. D. (1968). "Fulvenes and Substituted Fulvenes". Chemical Reviews. 68: 41–84. doi:10.1021/cr60251a002.
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.

Categories:

Latest revision as of 22:12, 3 September 2024

See also

References