9-Methylene-fluorene or dibenzofulvene (DBF) is a polycyclic aromatic hydrocarbon with chemical formula (C6H4)2C=CH2. It is best known as one product from deprotection of the Fmoc group.[1] It can be prepared by treatment of 9-hydroxymethylfluorene with strong base.[2]
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| Names | |
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| Preferred IUPAC name
9-Methylidene-9H-fluorene | |
| Other names
Methylenefluorene
9-Methylidenefluorene Dibenzofulvene | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.251.583 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C14H10 | |
| Molar mass | 178.234 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Properties
editIt is an analog of a 1,1-diphenylethylene. Polymerization of 9-methylene-fluorene produces a π-stacked polymer.[3]
See also
editReferences
edit- ^ Carpino, Louis A.; Han, Grace Y. (1972). "9-Fluorenylmethoxycarbonyl amino-protecting group". The Journal of Organic Chemistry. 37 (22): 3404–3409. doi:10.1021/jo00795a005.
- ^ Nakano, Tamaki; Nakagawa, Osamu; Yade, Tohru; Okamoto, Yoshio (2003). "Solid-State Polymerization of Dibenzofulvene Leading to a Copolymer with Oxygen". Macromolecules. 36 (5): 1433–1435. Bibcode:2003MaMol..36.1433N. doi:10.1021/ma025792r.
- ^ Tamaki Nakano; Kazuyuki Takewaki; Tohru Yade; Yoshio Okamoto (2001). "Dibenzofulvene, a 1,1-Diphenylethylene Analogue, Gives a π-Stacked Polymer by Anionic, Free-Radical, and Cationic Catalysts". J. Am. Chem. Soc. 123 (37): 9182–9183. doi:10.1021/ja0111131. PMID 11552835.
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