The effectivity of 1H-triazoles and -tetrazoles as activators in acid-catalyzed phosphoramidite alcoholysis



: Nurminen EJ, Mattinen JK, Lonnberg H

Publisher: WILEY-V C H VERLAG GMBH

: 2003

 Helvetica Chimica Acta

: HELVETICA CHIMICA ACTA

: HELV CHIM ACTA

: 86

: 6

: 2005

: 2008

: 4

: 0018-019X

DOI: https://doi.org/10.1002/hlca.200390157


The efficiency of 5-nitro-1,2,4-1H-triazole (3), 5-(methylthio)-1H-tetrazole (4), and 5-(4-nitrophenyl)-1H-tetrazole(5) as activators in phosphoramidite alcoholysis has been studied relative to 1H-tetrazole (6). Reactions of these azoles with diisopropyl (diisopropylamido)phosphite (1a) were followed in THF, and the rates were found to increase with increasing acidity of the azoles. The Bronsted a value of 0.7 determined for this dependence is in agreement with data published earlier.



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