Furan
Encyclopedia : F : FU : FUR : Furan
| Furan | |
|---|---|
| Chemical name | Furan |
| Chemical formula | C4H4O |
| Molecular mass | 68.07 g/mol |
| Melting point | −85.6 °C |
| Boiling point | 31.4 °C |
| Density | 0.936 g/cm3 |
| CAS number | 110-00-9 |
| SMILES | C1=CC=CO1 |
| |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) [Chemical infoboxInfobox disclaimer and references] | |
Furan is aromatic because one of the lone pairs of electrons on the oxygen atom is delocalized into the ring, creating a 4n+2 aromatic system (see Hückel's rule) similar to benzene. This aromatic system forms two rings of electrons above and below the flat structure with no discrete double bonds. The other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system.
Synthesis
- A classic furan organic synthesis is the Feist-Benary synthesis.
- One of the most simple synthesis methods for furans is the reaction of 1,4-diketones with diphosphorus pentoxide (P2O5) in the Paal-Knorr Synthesis. It is interesting that the thiophene formation reaction of 1,4-diketones with lawesson's reagent also forms furans as side products.
Reactions
- Due to its aromaticity, furan's behavior is quite dissimilar to that of the more typical heterocyclic ethers such as tetrahydrofuran. It is considerably more reactive than benzene in electrophilic substitution reactions.
- Furan is a diene in Diels-Alder reactions with electron-deficient dienophiles such as ethyl (E)-3-nitroacrylate.The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid Masesane I, Batsanov A, Howard J, Modal R, Steel P Beilstein Journal of Organic Chemistry, 2006 2:9 [Online Article] The reaction product is a mixture of isomers with preference for the endo isomer:
See also
- Tetrahydrofuran (THF), the fully hydrogenated analog of furan and a common solvent.
- Pyrrole, the nitrogen analog of furan.
- Thiophene, the sulfur analog of furan.
- Selenophene, the selenium analog of furan.
- Tellurophene, the Tellurium analog of furan.
- Benzofuran, furan with a fused benzene ring.
- Dibenzofuran, a compound class similar to dibenzodioxins.
- Simple aromatic rings
External links
References
From Wikipedia, the Free Encyclopedia. Original article here. Support Wikipedia by contributing or donating.
All text is available under the terms of the GNU Free Documentation License See Wikipedia Copyrights for details.