:9-Methylene-fluorene

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| ImageFile = 9-Methylene-fluorene.png

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| PIN = 9-Methylidene-9H-fluorene

| OtherNames = Methylenefluorene
9-Methylidenefluorene
Dibenzofulvene

| Section1 = {{Chembox Identifiers

| CASNo = 4425-82-5

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| PubChem = 78147

| ChemSpiderID = 70523

| SMILES = C=C1C2=CC=CC=C2C3=CC=CC=C13

| InChI= 1S/C14H10/c1-10-11-6-2-4-8-13(11)14-9-5-3-7-12(10)14/h2-9H,1H2

| InChIKey = ZYASLTYCYTYKFC-UHFFFAOYSA-N

| UNII = 9299E1P3CC

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| Section2 = {{Chembox Properties

| C=14|H=10

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9-Methylene-fluorene or dibenzofulvene (DBF) is a polycyclic aromatic hydrocarbon with chemical formula {{chem2|(C6H4)2C\dCH2}}. It is best known as one product from deprotection of the Fmoc group.{{cite journal |doi=10.1021/jo00795a005 |title=9-Fluorenylmethoxycarbonyl amino-protecting group |date=1972 |last1=Carpino |first1=Louis A. |last2=Han |first2=Grace Y. |journal=The Journal of Organic Chemistry |volume=37 |issue=22 |pages=3404–3409 }} It can be prepared by treatment of 9-hydroxymethylfluorene with strong base.{{cite journal |doi=10.1021/ma025792r |title=Solid-State Polymerization of Dibenzofulvene Leading to a Copolymer with Oxygen |date=2003 |last1=Nakano |first1=Tamaki |last2=Nakagawa |first2=Osamu |last3=Yade |first3=Tohru |last4=Okamoto |first4=Yoshio |journal=Macromolecules |volume=36 |issue=5 |pages=1433–1435 |bibcode=2003MaMol..36.1433N }}

Properties

It is an analog of a 1,1-diphenylethylene. Polymerization of 9-methylene-fluorene produces a π-stacked polymer.{{cite journal |author=Tamaki Nakano |author2=Kazuyuki Takewaki |author3=Tohru Yade |author4=Yoshio Okamoto | title = Dibenzofulvene, a 1,1-Diphenylethylene Analogue, Gives a π-Stacked Polymer by Anionic, Free-Radical, and Cationic Catalysts | journal = J. Am. Chem. Soc. | year = 2001 | volume = 123 | issue = 37 | pages = 9182–9183| doi = 10.1021/ja0111131 |pmid=11552835 }}

See also

References

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{{PAHs}}

{{DEFAULTSORT:Methylene-fluorene, 9-}}

Category:Fluorenes

Category:Polycyclic aromatic hydrocarbons

Category:Vinylidene compounds

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