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Protonation of phosphoramidites. The effect on nucleophilic displacement
Tekijät: Nurminen EJ, Mattinen JK, Lonnberg H
Kustantaja: ROYAL SOC CHEMISTRY
Julkaisuvuosi: 2000
Lehti:: Perkin 2
Tietokannassa oleva lehden nimi: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Lehden akronyymi: J CHEM SOC PERK T 2
Numero: 11
Aloitussivu: 2238
Lopetussivu: 2240
Sivujen määrä: 3
ISSN: 1470-1820
DOI: https://doi.org/10.1039/b004859n
Tiivistelmä
Phosphoramidites (1) have been protonated on the phosphorus atom by treatment with triflic acid and the properties and reactivity of the formed P-protonated species (2) have been studied. Cation 2 was found to react with alcohol more reluctantly than 1 in the presence of weak acids, which suggests that the fast acid-catalyzed alcoholysis of 1 must take place via N-protonation. Mechanisms of the nucleophilic displacement are discussed.
Phosphoramidites (1) have been protonated on the phosphorus atom by treatment with triflic acid and the properties and reactivity of the formed P-protonated species (2) have been studied. Cation 2 was found to react with alcohol more reluctantly than 1 in the presence of weak acids, which suggests that the fast acid-catalyzed alcoholysis of 1 must take place via N-protonation. Mechanisms of the nucleophilic displacement are discussed.
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