9-Methylene-fluorene explained

9-Methylene-fluorene or dibenzofulvene (DBF) is a polycyclic aromatic hydrocarbon with chemical formula . 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]

Properties

It is an analog of a 1,1-diphenylethylene. Polymerization of 9-methylene-fluorene produces a π-stacked polymer.^[3]

See also

• Fluorene
• Fluorenylmethyloxycarbonyl chloride
• Fluorenylidene

Notes and References

1. 10.1021/jo00795a005 . 9-Fluorenylmethoxycarbonyl amino-protecting group . 1972 . Carpino . Louis A. . Han . Grace Y. . The Journal of Organic Chemistry . 37 . 22 . 3404–3409 .
2. 10.1021/ma025792r . Solid-State Polymerization of Dibenzofulvene Leading to a Copolymer with Oxygen . 2003 . Nakano . Tamaki . Nakagawa . Osamu . Yade . Tohru . Okamoto . Yoshio . Macromolecules . 36 . 5 . 1433–1435 . 2003MaMol..36.1433N .
3. Tamaki Nakano . Kazuyuki Takewaki . Tohru Yade . Yoshio Okamoto . Dibenzofulvene, a 1,1-Diphenylethylene Analogue, Gives a π-Stacked Polymer by Anionic, Free-Radical, and Cationic Catalysts . J. Am. Chem. Soc. . 2001 . 123 . 37 . 9182–9183. 10.1021/ja0111131 . 11552835 .