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Nucleoside H-phosphonates. Part 19: Novel nucleotide analogues H-phosphonoselenoate mono- and diesters
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2002 Inngår i: Tetrahedron Letters, ISSN 0040-4039, Vol. 43, nr 3, s. 515-518Artikkel i tidsskrift (Fagfellevurdert) Published
sted, utgiver, år, opplag, sider
2002. Vol. 43, nr 3, s. 515-518
Identifikatorer
URN: urn:nbn:se:su:diva-24688OAI: oai:DiVA.org:su-24688DiVA, id: diva2:198114
Merknad
Part of urn:nbn:se:su:diva-736Tilgjengelig fra: 2005-11-11 Laget: 2005-11-11bibliografisk kontrollert
Inngår i avhandling
1. Studies on nucleoside H-phosphonoselenoate chemistry and chalcogen exchange reaction between P(V) and P(III) compounds
Åpne denne publikasjonen i ny fane eller vindu >>Studies on nucleoside H-phosphonoselenoate chemistry and chalcogen exchange reaction between P(V) and P(III) compounds
2005 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: Institutionen för organisk kemi, 2005. s. 38
Emneord
Phosphorus chemistry, H-phosphonate, H-phosphonoselenoate, nucleotide analogues, selenization, selenium transfer, phosphoroselenoate
HSV kategori
Identifikatorer
urn:nbn:se:su:diva-736 (URN)91-7155-163-8 (ISBN)
Disputas
2005-12-02, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Opponent
Veileder
Tilgjengelig fra: 2005-11-11 Laget: 2005-11-11bibliografisk kontrollert

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