Chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions via in situ generation of NOCl†

A combination of inorganic chloride salts [e.g. WCl6, AlCl3 and ZnCl2] and sodium nitrite in the presence of wet SiO2 were used as an effective nitrosating agent for the nitrosation of secondary amines to their corresponding nitroso derivatives under mild and heterogeneous conditions in moderate to excellent yields.

[1]  S. Salehzadeh,et al.  Synthesis and crystal structure determination of some asymmetrical and symmetrical CR-type macrocyclic Schiff base complexes, with a single pendant coordinating 2-aminoethyl arm. , 2000, Inorganic chemistry.

[2]  W. Scheidt,et al.  Structural and electronic characterization of nitrosyl(octaethylporphinato)iron(III) perchlorate derivatives. , 2000, Inorganic chemistry.

[3]  M. Zolfigol,et al.  Oxidation of 1,4-Dihydropyridines under Mild and Heterogeneous Conditions , 2000 .

[4]  M. Zolfigol,et al.  An Efficient Method for the Oxidation of Urazoles Under Mild and Heterogeneous Conditions , 2000 .

[5]  M. Zolfigol,et al.  An Efficient Method for N-Nitrosation of Secondary Amines Under Mild and Heterogeneous Conditions , 2000 .

[6]  M. Zolfigol,et al.  A Convenient Method for Selective Mono or Dinitration of Phenol under Mild Conditions , 2000 .

[7]  M. Zolfigol.  A Convenient Method for Production of Thionitrites and Disulfides Under Mild and Heterogeneous Condition , 2000 .

[8]  S. Salehzadeh,et al.  Nickel(II) and copper(II) complexes of macrocyclic and acyclic Schiff-base ligands derived from new asymmetrical tripodal tetraamines and 2,6-diacetylpyridine , 2000 .

[9]  M. Zolfigol,et al.  An Efficient Method for the Oxidation of Hantzsch 1,4-Dihydropyridines to their Corresponding Pyridine Derivatives Under Mild and Heterogeneous Conditions , 2000 .

[10]  S. Mallakpour,et al.  A Convenient Method for the Oxidation of Urazoles to Their Corresponding Triazolinediones Under Mild and Heterogeneous Conditions with Sodium Nitrite and Oxalic Dihydrate , 1999 .

[11]  M. Zolfigol,et al.  An Efficient Method for Production and Storage of Unstable S-Nitrosothiols Under Mild and Heterogeneous Condition with Sodium Nitrite and Oxalic Acid Dihydrate , 1999 .

[12]  M. Zolfigol.  Efficient and Chemoselective N-Nitrosation of Secondary Amines Under Mild and Heterogeneous Conditions with Sodium Nitrite and Oxalic Acid Two Hydrate , 1999 .

[13]  G. B. Richter‐Addo,et al.  Binding of Organic Nitroso Compounds to Metalloporphyrins , 1999 .

[14]  R. V. Parish,et al.  Isolation of ternary complex precursors and partially condensed␣intermediates to macrocyclic complexes of nickel(II) and copper(II) , 1998 .

[15]  R. V. Parish,et al.  Synthesis of an asymmetrical tripodal tetraamine ligand and its five-coordinate copper(II) complex , 1998 .

[16]  J D Young,et al.  Methods in Nitric Oxide Research , 1997 .

[17]  S. Patai.  The Chemistry of Amino, Nitroso, Nitro and Related Groups , 1996 .

[18]  K. Turnbull.  Bromination of sydnones. I. Reaction with 3‐arylsydnones containing electron‐donors on the aryl ring , 1985 .

[19]  J. Warner,et al.  N-nitrosamines via the phase-transfer mediated nitrosation of secondary amines with sodium nitrite and n-haloamides , 1984 .

[20]  H. Keypour,et al.  Macrocycle synthesis. CR-type complexes displaying pendant ligation and N3S coordination , 1979 .

[21]  T. Mabry,et al.  The Systematic Identification of Flavonoids , 1970, Springer Berlin Heidelberg.

[22]  R. Shriner.  The Systematic Identification of Organic Compounds: , 1936, Nature.