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Studies of Biomimtic Oxidations and Racemizations
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2004 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

This thesis deals with studies of ruthenium-catalyzed hydrogen transfer reactions for oxidations and racemization.

Through optimisation of the substrate-selective redox catalyst, the electron and proton transfer mediator (a benzoquinone derivative), and the oxygen-activating metal macrocycle a highly efficient biomimetic oxidation of secondary alcohols was obtained. Several alcohols were subjected to the new oxidation protocol and the corresponding ketones were isolated in high yield.

The deactivation of the oxygen-activating metal macrocycle retarded the aerobic oxidation of primary alcohols. Encapsulation of the metal macrocycle into zeolite, described in chapter 3, proved to be an efficient method to solve this problem and comparable conversion of alcohols was achieved. The immobilization of the oxygen-activating porphyrin to a surface can be an alternative approach to solve the deactivation problem. Therefore as the first step towards studies of immobilized porphyrins on a metal surface (of gold or silver), S-thioacetyl derivatized porphyrins were synthesized; two alternative syntheses are described in chapter 4.

A new and effecient ruthenium-catalyzed racemization protocol was established by proper ligand tuning. The racemization of the enantiomerically pure alcohols was increased significantly; this work is reported in chapter 5.

sted, utgiver, år, opplag, sider
Stockholm: Institutionen för organisk kemi , 2004. , s. 52
Emneord [en]
oxidation of alcohols, ruthenium, porphyrin, racemization
HSV kategori
Identifikatorer
URN: urn:nbn:se:su:diva-71ISBN: 91-7265-819-3 (tryckt)OAI: oai:DiVA.org:su-71DiVA, id: diva2:197629
Disputas
2004-04-01, Magnélisalen, Arrheniuslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Opponent
Veileder
Tilgjengelig fra: 2004-03-11 Laget: 2004-03-11 Sist oppdatert: 2013-08-15bibliografisk kontrollert
Delarbeid
1. Efficient Ruthenium-Catalyzed Aerobic Oxidation of Alcohols Using a Biomimetic Coupled Catalytic System
Åpne denne publikasjonen i ny fane eller vindu >>Efficient Ruthenium-Catalyzed Aerobic Oxidation of Alcohols Using a Biomimetic Coupled Catalytic System
Vise andre…
2002 Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, Vol. 67, nr 5, s. 1657-1662Artikkel i tidsskrift (Fagfellevurdert) Published
Identifikatorer
urn:nbn:se:su:diva-24476 (URN)
Merknad
Part of urn:nbn:se:su:diva-71Tilgjengelig fra: 2004-03-11 Laget: 2004-03-11bibliografisk kontrollert
2. Ruthenium-Catalyzed Aerobic Oxidation of Alcohols on Zeolite-Encapsulated Cobalt Salophen Catalyst
Åpne denne publikasjonen i ny fane eller vindu >>Ruthenium-Catalyzed Aerobic Oxidation of Alcohols on Zeolite-Encapsulated Cobalt Salophen Catalyst
2002 Inngår i: Topics in catalysis, ISSN 1022-5528, Vol. 19, nr 1, s. 119-124Artikkel i tidsskrift (Fagfellevurdert) Published
Identifikatorer
urn:nbn:se:su:diva-24477 (URN)
Merknad
Part of urn:nbn:se:su:diva-71Tilgjengelig fra: 2004-03-11 Laget: 2004-03-11bibliografisk kontrollert
3. Synthesis os S-Thioacetate Functionalized Cobalt(II) Porphyrins and Heterogenization on gold Surface
Åpne denne publikasjonen i ny fane eller vindu >>Synthesis os S-Thioacetate Functionalized Cobalt(II) Porphyrins and Heterogenization on gold Surface
Vise andre…
2006 (engelsk)Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, nr 5, s. 1193-1199Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Cobalt tetraarylporphyrins 1-Co and 2-Co with thioacetate-functionalized carbon chains on the aryl groups were synthesized. The cobalt porphyrin 2-Co was immobilized on a gold surface after deprotection of the S-acetyl group. The immobilized porphyrin was studied by X-ray Photoelectron Spectroscopy (XPS) and the results suggest that a complete monolayer of porphyrins is formed.

sted, utgiver, år, opplag, sider
Wiley-VCH Verlagsgesellschaft, 2006
Emneord
functionalized porphyrin, immobilization, gold surface, monolayers, photoelectron spectroscopy
HSV kategori
Identifikatorer
urn:nbn:se:su:diva-24478 (URN)10.1002/ejoc.200500656 (DOI)
Merknad

Part of urn:nbn:se:su:diva-71

Tilgjengelig fra: 2004-03-11 Laget: 2004-03-11 Sist oppdatert: 2017-12-13bibliografisk kontrollert
4. New Efficient Ruthenium Catalysts for Racemization of Alcohols at Room Temperature
Åpne denne publikasjonen i ny fane eller vindu >>New Efficient Ruthenium Catalysts for Racemization of Alcohols at Room Temperature
2004 (engelsk)Inngår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 45, nr 36, s. 6799-6802Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

5-Pentaphenylcyclopentadienyl)RuCl(CO)2 was found to catalyze efficiently the racemization of chiral alcohols such as (S)-1-phenylethanol, (S)-1-phenylpropan-2-ol, (S)-4-phenylbutan-2-ol and (S)-4-methoxy-1-phenylethanol at room temperature in the presence of a base. The catalytic activity of three other Ru(II) complexes was also investigated. The effects of halide and solvent were studied as well.

HSV kategori
Identifikatorer
urn:nbn:se:su:diva-24330 (URN)10.1016/j.tetlet.2004.07.013 (DOI)
Tilgjengelig fra: 2007-05-30 Laget: 2007-05-23 Sist oppdatert: 2017-12-13bibliografisk kontrollert

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