9-Methylene-fluorene

9-Methylene-fluorene
Names
	Preferred IUPAC name 9-Methylidene-9H-fluorene
	Other names Methylenefluorene; 9-Methylidenefluorene; Dibenzofulvene
Identifiers
CAS Number	4425-82-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	70523;
ECHA InfoCard	100.251.583
PubChem CID	78147;
UNII	9299E1P3CC;
CompTox Dashboard (EPA)	DTXSID90196082 ;
	InChI InChI=1S/C14H10/c1-10-11-6-2-4-8-13(11)14-9-5-3-7-12(10)14/h2-9H,1H2 Key: ZYASLTYCYTYKFC-UHFFFAOYSA-N;
	SMILES C=C1C2=CC=CC=C2C3=CC=CC=C13;
Properties
Chemical formula	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). Infobox references

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]

Properties

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

References

^ 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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[1] 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.

[2] 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.

[3] 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.

[1]

[2]

[3]

v t e Polycyclic aromatic hydrocarbons
2 rings	Butalene Azulene Naphthalene
3 rings	Acenaphthene Acenaphthylene Anthracene Fluorene Phenalene Phenanthrene
4 rings	Benz[a]anthracene Benzo[a]fluorene Benzo[c]fluorene Benzo[c]phenanthrene Chrysene Fluoranthene Pyrene Tetracene Triphenylene Tricyclobutabenzene
5 rings	Benz[e]acephenanthrylene Benzopyrene Benzo[a]pyrene Benzo[e]pyrene 6H-Benzo[cd]pyrene(Olympicene) Benzo[a]fluoranthene Benzo[b]fluoranthene Benzo[j]fluoranthene Benzo[k]fluoranthene trans-Bicalicene Dibenz[a,h]anthracene Dibenz[a,j]anthracene Pentacene Pentaphene Perylene Picene Tetraphenylene
6 rings	Anthanthrene Benzo[ghi]perylene Corannulene Dibenzopyrenes Hexacene Triangulene Zethrene
7+ rings	Coronene Dicoronylene Diindenoperylene Heptacene Hexabenzocoronene (Hexa-cata-) Kekulene Ovalene Rubicene Rubrene Sumanene Superphenalene Trinaphthylene Truxene
General classes	Acene Circulene Cyclacene Helicene Phenacene

Properties

See also

References