Benzopyran

From Wikipedia, the free encyclopedia
Benzopyran
Identifiers

 ChemSpider 10651828 YesY
Properties
Molecular formula C9H8O
Molar mass 132.16 g mol−1
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Benzopyran is an polycyclic organic compound that results from the fusion of a benzene ring to a heterocyclic pyran ring. According to IUPAC nomenclature it is called chromene. There are two isomers of benzopyran that vary by the orientation of the fusion of the two rings compared to the oxygen, resulting in 1-benzopyran (chromene) and 2-benzopyran (isochromene)—the number denotes where the oxygen atom is located by standard naphthalene-like nomenclature.

The radical form of benzopyran is paramagnetic. The unpaired electron is delocalized over the whole benzopyran molecule, rendering it less reactive than one would expect otherwise, a similar example is the cyclopentadienyl radical. Commonly, benzopyran is encountered in the reduced state, in which it is partially saturated with one hydrogen atom, introducing a tetrahedral CH2 group in the pyran ring. Therefore, there are many structural isomers owing to the multiple possible positions of the oxygen atom and the tetrahedral carbon atom:

Structural isomers of chromene

2H-chromene
(2H-1-benzopyran)

4H-chromene
(4H-1-benzopyran)
5H-chromene
7H-chromene
8aH-chromene
Structural isomers of isochromene

1H-isochromene
(1H-2-benzopyran)

3H-isochromene
(3H-2-benzopyran)

See also

References

    This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.