N-Hydroxyphthalimide: What Else Can You Ask For?

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.

References

• 1 Barlaam B. Hamon A. Maudet M. Tetrahedron Lett.  1998,  39:  7865 
• 2 Ishii Y. Sakaguchi S. Iwahama T. Adv. Synth. Catal.  2001,  343:  393 
• 3 Minisci F. Porta O. Recupero F. Gambarotti C. Paganelli R. Pedulli GF. Fontana F. Tetrahedron Lett.  2004,  45:  1607 
• 4 Sakaguchi S. Hirabayashi T. Ishii Y. Chem. Commun.  2002,  516 
• 5a Yoshino Y. Hayashi Y. Iwahama T. Sakaguchi S. Ishii Y. J. Org. Chem.  1997,  62:  6810 
• 5b Tashiro Y. Iwahama T. Sakaguchi S. Ishii Y. Adv. Synth. Catal.  2001,  343:  220 
• 6 Karimi B. Rajabi J. Synthesis  2003,  2373 
• 7 Minisci F. Gambarotti C. Pierini M. Porta O. Punta C. Recupero F. Lucarini M. Mugnaini V. Tetrahedron Lett.  2006,  47:  1421 
• 8 Iwahama T. Sakaguchi S. Ishii Y. Tetrahedron Lett.  1998,  39:  9059 
• 9 Fieser LF. Fieser M. Reagents for Organic Synthesis   Wiley; New York: 1967.  p.485 
• 10 inventors; Fritz-Langhals E. UPS  6316639. 
• 11 Maillard LT. Benohoud M. Durand P. Badet B. J. Org. Chem.  2005,  70:  6303 
• 12 Tayama O. Iwahama T. Sakaguchi S. Ishii Y. Eur. J. Org. Chem.  2003,  2286 
• 13 Eikawa M. Sakaguchi S. Ishii Y. J. Org. Chem.  1999,  64:  4676 
• 14 Tsujimoto S. Sakaguchi S. Ishii Y. Tetrahedron Lett.  2003,  44:  5601 
• 15 Ishii Y. Sakaguchi S. Nishiwaki Y. Kitamura T. Angew. Chem. Int. Ed.  2001,  40:  222