Regiospecific synthesis of disubstituted phenanthrenes
Master thesis
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http://hdl.handle.net/11250/224230Utgivelsesdato
2014-06-16Metadata
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Sammendrag
As the Norwegian oil fields mature, the wells produce more water. This produced
water containing a diverse mixture of dissolved PAHs is eventually released to the environment.
A major part of these discharges are alkylated PAHs, but due to lack of
pure compounds the e↵ect of alkylated PAHs have been scarcely studied. Studies on
the metabolism of monomethylated phenanthrenes by the benthic invertebrate Nereis
diversicolor gave di↵erent product distributions depending on the position of the substituent.
Now various dimethylated phenanthrenes are needed for further environmental
studies. In this thesis a selection of dimethylated phenanthrenes has been prepared using
a combination of Directed ortho-Metalation (DoM), Suzuki-Miyaura cross coupling, and
Directed remote-Metalation (DreM). 2,7-, 2,3-, 1,7- and 2-6-dimethyl-9-phenanthrol have
been made into the corresponding phenanthrenes by a simple Pd-catalyzed hydrogenolysis
of the triflate protected alcohol. The single isomers resulting from this route provides
the dimethylphenanthrenes in high purity and in gram quantities,
Beskrivelse
Master's thesis in Biological chemistry