(1H-BENZOTRIAZOL-1-YLOXY)TRIS(DIMETHYLAMINO)PHOSPHONIUM HEXAFLUOROPHOSPHATE-MEDIATED AND (1H-BENZOTRIAZOL-1-YLOXY)TRIPYRROLIDINOPHOSPHONIUM HEXAFLUOROPHOSPHATE-MEDIATED ACTIVATION OF MONOPHOSPHONATE ESTERS - SYNTHESIS OF MIXED PHOSPHONATE DIESTERS, THE REACTIVITY OF THE BENZOTRIAZOLYL PHOSPHONIC ESTERS VS THE REACTIVITY OF THE BENZOTRIAZOLYL CARBOXYLIC ESTERS

被引：53

作者：

CAMPAGNE, JM

COSTE, J

JOUIN, P

机构：

[1] Department of Chemistry, Stanford University, Stanford

[2] Laboratoire des Mécanismes Moléculaires des Communications Cellulaires, Centre CNRS-INSERM de Pharmacologie-Endocrinologie, 34094 Montpellier Cedex 5, Rue de la Cardonille

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 16期

关键词：

D O I：

10.1021/jo00121a045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method for synthesizing mixed phosphonate diesters from monoesters using (1H-benzotriazol-1-yloxy)tris(dimethylamino) hexafluorophosphate or (1H-benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate reagents is described. The reaction proceeded through a benzotriazolyl ester as shown by comparison with other reagents such as DCC, DCC/DMAP, DCC/1-hydroxybenzotriazole, bromotris(dimethylamino)phosphonium hexafluorophosphate, or O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate and by P-31 NMR analysis. This benzotriazolyl phosphonic ester intermediate was more reactive toward alcohols than toward amines, contrary to its carboxylic analogue.

引用

页码：5214 / 5223

页数：10

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