:9-Methylene-fluorene
{{Chembox
| ImageFile = 9-Methylene-fluorene.png
| ImageSize =
| PIN = 9-Methylidene-9H-fluorene
| OtherNames = Methylenefluorene
9-Methylidenefluorene
Dibenzofulvene
| Section1 = {{Chembox Identifiers
| CASNo = 4425-82-5
| CASNo_Ref = {{cascite|correct|CAS}}
| 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
}}
| Section2 = {{Chembox Properties
| C=14|H=10
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
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
{{reflist}}
{{PAHs}}
{{DEFAULTSORT:Methylene-fluorene, 9-}}
Category:Polycyclic aromatic hydrocarbons
{{Hydrocarbon-stub}}