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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 is used to make dyes, plastics, pesticides, explosives, and drugs. It has also been used to make bile acids, cholesterol and steroids. [3] Phenanthrene occurs naturally and also is a man-made chemical. Commonly, humans are exposed to phenanthrene through inhalation of cigarette smoke, but there are many routes of exposure.
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.
The carbene is a tungsten carbonyl when used in stoichiometric amounts (1 equivalent) yields 41% of the phenanthrene 3.2 and when used in catalytic amounts phenanthrene 3.3. The stereoselectivity of this reaction is large with the metal atom exclusively adding to one of the alkyne carbon atoms in the initial reaction step.
Diphenic acid is prepared from anthranilic acid by diazotization, followed by reduction with copper(I). [4]It can also be synthesized from the oxidation of phenanthrene by peracetic acid, which is first prepared from acetic acid and 90% hydrogen peroxide: [5]
The oxirane is first converted into a 2-azidoalcohol with the use of an azide such as sodium azide.The azido alcohol is then reduced with the use of a trialkylphosphine such as triphenylphosphine in a manner similar to the Staudinger reaction, concomitant with loss of N 2.
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]
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 +).