The Effectivity of 1 H ‐Triazoles and ‐Tetrazoles as Activators in Acid‐Catalyzed Phosphoramidite Alcoholysis

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...

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Bibliographic Details
Published in:Helvetica chimica acta 2003-06, Vol.86 (6), p.2005-2008
Main Authors: Nurminen, Erkki. J., Mattinen, Jorma K., Lönnberg, Harri
Format: Article
Language:English
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Summary: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.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200390157