Phenanthrene

From Wikipedia, the free encyclopedia

Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings--as the above formula shows. The name Phenanthrene is a composite of phenyl and anthracene. It provides the framework for the Steroids. In its pure form, it is found in cigarette smoke and is a known carcinogen.

1 Chemistry
- 1.1 Canonical forms of Phenanthrene
2 External links
3 References

[edit] Chemistry

A classical phenanthrene synthesis is the Bardhan-Sengupta Phenanthrene Synthesis (1932) <ref>chempensoftware.com Link</ref>. In the second step of this reaction 9,10-dihydrophenanthrene is oxidized with elemental selenium.

Reactions of phenanthrene typically occur at the 9 and 10 positions. Some bacic reactions:

Organic oxidation to Phenanthrenequinone with chromic acid <ref>Organic Syntheses, Coll. Vol. 4, p.757 (1963); Vol. 34, p.76 (1954) Link</ref>
Organic reduction to 9,10-dihydrophenanthrene with hydrogen gas and raney nickel <ref> Organic Syntheses, Coll. Vol. 4, p.313 (1963); Vol. 34, p.31 (1954) Link.</ref>
Electrophilic halogenation to 9-bromophenanthrene with bromine <ref>Organic Syntheses, Coll. Vol. 3, p.134 (1955); Vol. 28, p.19 (1948) Link.</ref>
Aromatic sulfonation to 2 and 3-phenanthrenesulfonic acids with sulfuric acid <ref>Organic Syntheses, Coll. Vol. 2, p.482 (1943); Vol. 16, p.63 (1936) Link.</ref>
Ozonolysis to diphenylaldehyde <ref>Organic Syntheses, Coll. Vol. 5, p.489 (1973); Vol. 41, p.41 (1961) Link.</ref>