A1 Refereed original research article in a scientific journal
Protonation of phosphoramidites. The effect on nucleophilic displacement
Authors: Nurminen EJ, Mattinen JK, Lonnberg H
Publisher: ROYAL SOC CHEMISTRY
Publication year: 2000
Journal:: Perkin 2
Journal name in source: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Journal acronym: J CHEM SOC PERK T 2
Issue: 11
First page : 2238
Last page: 2240
Number of pages: 3
ISSN: 1470-1820
DOI: https://doi.org/10.1039/b004859n
Abstract
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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