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The Effectivity of 1 H ‐Triazoles and ‐Tetrazoles as Activators in Acid‐Catalyzed Phosphoramidite Alcoholysis
Author(s) -
Nurminen Erkki. J.,
Mattinen Jorma K.,
Lönnberg Harri
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390157
Subject(s) - phosphoramidite , chemistry , tetrazole , catalysis , medicinal chemistry , organic chemistry , combinatorial chemistry , biochemistry , dna , oligonucleotide
Abstract The efficiency of 5‐nitro‐1,2,4‐1 H ‐triazole ( 3 ), 5‐(methylthio)‐1 H ‐tetrazole ( 4 ), and 5‐(4‐nitrophenyl)‐1 H ‐tetrazole ( 5 ) as activators in phosphoramidite alcoholysis has been studied relative to 1 H ‐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 Brønsted α value of 0.7 determined for this dependence is in agreement with data published earlier.