Tetrahedron Letters

Reaction of triflyl-imidazole with aldoximes: facile synthesis of nitriles and formation of novel aldoxime-bis (N-triflyl)-imidazole adducts

RG Kalkhambkar, SD Bunge, KK Laali

Index: Kalkhambkar, Rajesh G.; Bunge, Scott D.; Laali, Kenneth K. Tetrahedron Letters, 2011 , vol. 52, # 40 p. 5184 - 5187

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Citation Number: 14

Abstract

The synthetic utility of N-triflylimidazole as an in situ reagent for facile, high yielding, synthesis of various aliphatic, aromatic, and heteroaromatic nitriles from the corresponding aldoximes has been demonstrated. With benzaldoximes, in the presence of certain substitutents (2-F; 2-OMe; 3-CF3; 2-Me-5-F) a different course of reaction was observed, leading instead to novel 1: 1 aldoxime-bis (N-triflyl) imidazole covalent adducts, in which ...