NMR Studies and electrophilic properties of triphenylphosphine-trifluoromethanesulfonic anhydride; a remarkable dehydrating reagent system for the conversion of aldoximes into nitriles

被引：23

作者：

Moussa, Ziad ^{[1
]}

Ahmed, Saleh A. ^{[1
]}

ElDouhaibi, Ahmad S. ^{[1
]}

Al-Raqa, Shaya Y. ^{[1
]}

机构：

[1] Taibah Univ, Fac Sci, Dept Chem, Almadinah Almunawarrah, Saudi Arabia

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 14期

关键词：

Aldoximes; Nitriles; Dehydration; Triphenylphosphine; Triflic anhydride; Triphenyl(trifluoromethylsulfonyloxy)-phosphonium trifluoromethanesulfinate; Bis(triphenyl)oxodiphosphonium trifluoromethanesulfinate; AMIDES;

D O I：

10.1016/j.tetlet.2010.01.119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

NMR Studies on the reaction of triphenylphosphine with various amounts of triflic anhydride at 0 degrees C is described. The reagent structure resulting from mixing 1.3 equiv of Ph(3)P with Tf(2)O (1.0 mmol) has been established as an equilibrium mixture consisting mainly of triphenyl(trifluoromethylsulfonyloxy)phosphonium trifluoromethanesulfinate and the corresponding bis(triphenyl)oxodiphosphonium trifluoromethanesulfinate dimer. The electrophilic properties of the system have been exploited in the development of a mild method for converting aldoximes into nitriles. The dehydration occurs at 0 degrees C under very mild conditions by initial activation of the oxime oxygen, followed by treatment with a base and subsequent elimination of triphenylphosphine oxide. The substrate scope and functional group tolerance of this useful method are explored. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1826 / 1831

页数：6