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Nucleoside H-phosphonates XX: Efficient method for the preparation of nucleoside H-phosphonoselenoate monoesters
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2005 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 10, 1668-1674 p.Article in journal (Refereed) Published
Place, publisher, year, edition, pages
2005. no 10, 1668-1674 p.
National Category
Organic Chemistry
URN: urn:nbn:se:su:diva-24690DOI: 10.1055/s-2005-865300ISI: 000230380900020OAI: diva2:198116

Part of urn:nbn:se:su:diva-736

Available from: 2005-11-11 Created: 2005-11-11 Last updated: 2015-10-14Bibliographically approved
In thesis
1. Studies on nucleoside H-phosphonoselenoate chemistry and chalcogen exchange reaction between P(V) and P(III) compounds
Open this publication in new window or tab >>Studies on nucleoside H-phosphonoselenoate chemistry and chalcogen exchange reaction between P(V) and P(III) compounds
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In this thesis, the chemistry of compounds containing P-Se bonds has been studied. As a new addition to this class of compounds, H-phosphonoselenoate monoesters, have been introduced and two synthetic pathways for their preparation have been developed.

The reactivity of H-phosphonoselenoate monoesters towards a variety of condensing agents has been studied. From these, efficient conditions for the synthesis of H-phosphonoselenoate diesters have been developed. The produced diesters have subsequently been used in oxidative transformations, which gave access to the corresponding P(V) compounds, e.g. dinucleoside phosphoroselenoates or dinucleoside phosphoroselenothioates.

Furthermore, a new selenizing agent, triphenyl phosphoroselenoate, has been developed for selenization of P(III) compounds. This reagent has high solubility in organic solvents and was found to convert phosphite triesters and H-phosphonate diesters efficiently into the corresponding phosphoroselenoate derivatives.

The selenization of P(III) compounds with triphenyl phosphoroselenoate proceeds through a selenium transfer reaction. A computational study was performed to gain insight into a mechanism for this reaction. The results indicate that the transfer of selenium or sulfur from P(V) to P(III) compounds proceeds most likely via an X-philic attack of the P(III) nucleophile on the chalcogen of the P(V) species. For the transfer of oxygen, the reaction may also proceed via an edge attack on the P=O bond.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2005. 38 p.
Phosphorus chemistry, H-phosphonate, H-phosphonoselenoate, nucleotide analogues, selenization, selenium transfer, phosphoroselenoate
National Category
Organic Chemistry
urn:nbn:se:su:diva-736 (URN)91-7155-163-8 (ISBN)
Public defence
2005-12-02, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Available from: 2005-11-11 Created: 2005-11-11Bibliographically approved

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