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Benzylic C–H oxidations of dehydroabietic acid derivatives at positions 7 and 15

Show simple item record 2016-10-05T12:44:33Z und 2017-10-24T12:19:21Z 2016-10-05T12:44:33Z und 2017-10-24T12:19:21Z 2016-10-05T12:44:33Z
dc.identifier.uri und
dc.title Benzylic C–H oxidations of dehydroabietic acid derivatives at positions 7 and 15 en
ethesis.discipline Organic chemistry en
ethesis.discipline Orgaaninen kemia fi
ethesis.discipline Organisk kemi sv
ethesis.department Kemiska institutionen sv
ethesis.department Department of Chemistry en
ethesis.department Kemian laitos fi
ethesis.faculty Matematisk-naturvetenskapliga fakulteten sv
ethesis.faculty Matemaattis-luonnontieteellinen tiedekunta fi
ethesis.faculty Faculty of Science en
ethesis.faculty.URI Helsingfors universitet sv University of Helsinki en Helsingin yliopisto fi
dct.creator Krogerus, Sara
dct.issued 2016
dct.language.ISO639-2 eng
dct.abstract Dehydroabietic acid is a natural diterpene readily available from disproportionated rosin. This natural product has attracted the interest of both the synthetic, medical and pharmacological communities due to the wide variety of important biological activities it exhibits. In search for potent pharmaceutical agents, numerous derivatives of dehydroabietic acid have been designed and synthesized accordingly. One key reaction in such syntheses is the benzylic oxidation of positions 7 and 15 in the dehydroabietane core. The oxidized derivatives act as key intermediates in the synthesis of both natural and unnatural dehydroabietanes and related compounds. In the literature part of this thesis, known methods for the benzylic C–H oxidation of dehydroabietanes are presented. In the majority of these methods noxious Cr(VI) compounds are required which produce large amounts of toxic waste. The growing concern on the environmental impact of chemicals has led to an increasing interest towards developing environmentally friendlier oxidation procedures, using cheap and readily available oxidants. Recently, much research has focused on the development of transition metal free approaches for benzylic C–H oxidation. The topic is also discussed in this thesis. In the experimental part transition metal free methods for the benzylic oxidation of dehydroabietic acid derivatives are investigated. An environmentally friendly procedure using sodium chlorite in the presence of aqueous tert-butyl hydroperoxide is described. This procedure resulted in the formation of several variously oxygenated dehydroabietic derivatives which were characterized by IR, NMR and HRMS spectrometry. A manuscript is being prepared based on some of the results presented in this thesis. en
dct.language en
ethesis.language English en
ethesis.language englanti fi
ethesis.language engelska sv
ethesis.thesistype pro gradu-avhandlingar sv
ethesis.thesistype pro gradu -tutkielmat fi
ethesis.thesistype master's thesis en
dct.identifier.urn URN:NBN:fi-fe2017112251534
dc.type.dcmitype Text

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