Synthesis 2003(10): 1591-1597
DOI: 10.1055/s-2003-40518
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Selective N-Nitrosation of Amines, N-Alkylamides and N-Alkylureas by N2O4 Supported on Cross-Linked Polyvinylpyrrolidone (PVP-N2O4)

Nasser Iranpoor*, Habib Firouzabadi*, Ali-Reza Pourali
Department of Chemistry, Shiraz University, Shiraz 71454, Iran
Fax: +98(711)2280926; e-Mail: iranpoor@chem.susc.ac.ir; firouzabadi@chem.susc.ac.ir.;
Further Information

Publication History

Received 3 March 2003
Publication Date:
08 July 2003 (online)

Abstract

N2O4 was supported on the cross-linked polyvinylpyrrolidone (PVP) to afford a solid, stable and recyclable nitrosating agent. This reagent shows excellent selectivity for N-nitrosation of dialkyl amines in the presence of diaryl-, arylalkyl-, trialkylamines and also for secondary amides in dichloromethane at room temperature under mild and heterogeneous conditions. Also N-nitroso-N-alkyl amides can be selectively prepared in the presence of primary amides and N-phenylamides under similar reaction conditions. Selective N-nitrosation or dealkylation and N-nitrosation of tertiary amines can also be performed by this reagent.