Protonation of phosphoramidites. The effect on nucleophilic displacement



: Nurminen EJ, Mattinen JK, Lonnberg H

Publisher: ROYAL SOC CHEMISTRY

: 2000

Perkin 2

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2

: J CHEM SOC PERK T 2

: 11

: 2238

: 2240

: 3

: 1470-1820

DOI: https://doi.org/10.1039/b004859n


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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