Issue 11, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Protonation of phosphoramidites. The effect on nucleophilic displacement

Erkki J. Nurminen,*a   Jorma K. Mattinena  and  Harri Lönnbergb  

* Corresponding authors

a Department of Organic Chemistry, Åbo Akademi University, Åbo, Finland

b Department of Chemistry, Turku University, Turku, Finland

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 viaN-protonation. Mechanisms of the nucleophilic displacement are discussed.

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Article information

DOI
https://doi.org/10.1039/B004859N
Article type
Paper
Submitted
19 Jun 2000
Accepted
17 Aug 2000
First published
19 Oct 2000

J. Chem. Soc., Perkin Trans. 2, 2000, 2238-2240

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Protonation of phosphoramidites. The effect on nucleophilic displacement

E. J. Nurminen, J. K. Mattinen and H. Lönnberg, J. Chem. Soc., Perkin Trans. 2, 2000, 2238 DOI: 10.1039/B004859N

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