Synlett 2011(1): 141-142  
DOI: 10.1055/s-0030-1259278
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

N-Hydroxyphthalimide: What Else Can You Ask For?

Leonardo X. Alvarez*
Département de Chimie Moléculaire (SERCO), UMR-5250, ICMG FR-2607, Université Joseph Fourier, 301 Rue de la Chimie, BP 53, 38401 Grenoble, Cedex 9, France
e-Mail: Leonardo.Alvarez@ujf-grenoble.fr;
Further Information

Publication History

Publication Date:
14 December 2010 (online)

Introduction

N-Hydroxypthalimide (1, NHPI, Figure  [¹] ) is a white crystalline powder that has been used for the preparation of O-alkyl hydroxylamines, [¹] the functionalization of alkenes, [²] the halogenation of alkanes, [³] the Ritter-type reactions of alkylbenzenes, [4] and for the oxidation of alkylbenzenes, [5] acetals, [6] alkenes, [7] and sulfides [8] . Some other applications are described below.

Figure 1

This reagent is not very expensive, it is air-stable, and does not need particular conditions for storage, but precautions must be taken for its manipulation, because it can be very irritating to the eyes and the skin.