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Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with formula C 14 H 10, ... Oxidation with chromic acid gives gives phenanthrenequinone. [11]
Oxidation of 1,10-phenanthroline with a mixture of nitric and sulfuric acids gives 1,10-phenanthroline-5,6-dione. [6] 1,10-Phenanthroline forms many coordination complexes. One example is the iron complex called ferroin. Alkyllithium reagents form deeply colored derivatives with phenanthroline.
It has been prepared by oxidation of phenanthrene with chromic acid. [3] It is used as an artificial mediator for electron acceptor/donor in Mo/W containing formate dehydrogenase reduction of carbon dioxide to formate and vice versa. It is a better electron acceptor than the natural nicotinamide adenine dinucleotide (NAD +).
ortho-Substituted substrates generally give 1-substituted phenanthrenes, unless the substituent is a good leaving group, in which case elimination to form unsubstituted phenanthrene occurs. [11] meta- Substituted substrates give mixtures of 2- and 4-substituted products. Substitution of the exocyclic double bond is well tolerated.
Phenanthrene can also be treated with other oxidizing agents (such as hydrogen peroxide, chromium trioxide, potassium dichromate, or potassium permanganate), which first yields phenanthrenequinone and gives diphenic acid on further oxidation.
DDQ and an acid catalyst has been used to synthesise a steroid with a phenanthrene core by oxidation accompanied by a double methyl migration. [9] In the process, DDQ is itself reduced into an aromatic hydroquinone product. Sulfur and selenium are traditionally used in aromatization, the leaving group being hydrogen sulfide. [10]
The Bogert–Cook synthesis (1933) involves the dehydration and isomerization of 1-β-phenylethylcyclohexanol to the octahydro derivative of phenanthrene [23] The Darzens–Nenitzescu synthesis of ketones (1910, 1936) involves the acylation of cyclohexene with acetyl chloride to methylcyclohexenylketone.
Nudol is a phenanthrene from the orchids Eulophia nuda, Eria carinata and Eria stricta. [10] 9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol is a phenanthrene from Eulophia nuda. This compound shows cytotoxic activity against human cancer cells. [11] 2,7-Dihydroxy-3,6-dimethoxyphenanthrene is a phenanthrene from Dehaasia longipedicellata. [12]