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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 4
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Original Articles

Bismuth Chloride–Sodium Nitrite: A Novel Reagent for Chemoselective N-Nitrosation

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Pages 604-612 | Received 11 Jun 2008, Published online: 27 Jan 2009

REFERENCES

  • Moncada , S. ; Palmer , R. M. ; Higgs , E. A. Nitric oxide: Physiology, pathophysiology, and pharmacology . Pharmacol. Rev. 1991 , 43 , 109 .
  • Kostyukovskii , Y. L. ; Melamed , D. B. Carcinogenic N-nitrosamines: Formation, properties, and analysis . Russ. Chem. Rev. 1988 , 57 , 350 .
  • Seebach , D. ; Wykypiel , W. Safe one-pot carbon-carbon bond formation with lithiated nitrosamines including denitrosation by sequential reduction with lithium aluminium hydride and Raney-nickel. Synthesis 1979, 423.
  • Touster , O. Determination of keto–enol equilibrium constants and the kinetic study of the nitrosation reaction of β-dicarbonyl compounds . In Organic Reactions ; Wiley : New York , 1953 ; vol. 7, chap 6 .
  • Williams , D. L. H. Nitrosation Reactions and the Chemistry of Nitric Oxide, , 1st ed. ; Elsevier Science : Amsterdam , Oxford , 2004 .
  • Garcia Rio , L. ; Leis , J. R. ; Iglesias , E. Nitrosation of amines in nonaqueous solvents, 1: Evidence of a stepwise mechanism . J. Org. Chem. 1997 , 62 , 4701 .
  • Leis , J. R. ; Peña , M. E. ; Rios , A. M. Nucleophilic reactivity towards ‘normal’ and ambidentate electrophiles bearing the nitroso group A . J. Chem. Soc., Perkin Trans. 2 1995 , 587 .
  • Uppu , R. M. ; Squadrito , G. L. ; Bolzan , R. M. ; Pryor , W. A. Nitration and nitrosation by peroxynitrite: Role of CO2 and evidence for common intermediates . J. Am. Chem. Soc. 2000 , 122 , 6911 .
  • Castedo , L. ; Riguera , R. ; Vazquez , M. P. Fremy's salt (potassium nitrosodisulphonate): A nitrosating reagent for amines . J. Chem. Soc. Chem. Commun. 1983 , 301 .
  • Chang , S. K. ; Harrington , G. W. ; Rothstein , M. ; Shergalis , W. A. ; Swern , D. ; Vohra , S. K. Accelerating effect of ascorbic acid on N-nitrosamine formation and nitrosation by oxyhyponitrite . Cancer Res. 1979 , 39 , 3871 .
  • Cova , D. ; Nebuloni , C. ; Arnoldi , A. ; Bassoli , A. ; Trevisan , M. ; Del Re , A. A. M. N-Nitrosation of triazines in human gastric juice . J. Agric. Food. Chem. 1996 , 44 , 2852 .
  • Zolfigol , M. A. ; Habibi , D. ; Mirjalili , B. F. ; Bamoniri , A. The use of Nafion-H®/NaNO2 as an efficient procedure for the chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions . Tetrahedron Lett. 2003 , 44 , 3345 .
  • Zolfigol , M. A. ; Zabarjadian , M. H. ; Chehardoli , G. ; Keypour , H. ; Salehzadeh , S. ; Shamsipur , M. N-Nitrosation of secondary amines with [NO+ · crown · H(NO3)2 −] . J. Org. Chem. 2001 , 66 , 3619 .
  • Iranpoor , N. ; Firouzabadi , H. ; Pourali , A.-R. Selective N-nitrosation of amines, N-alkylamides, and N-alkylureas by N2O4 supported on cross-linked polyvinylpyrrolidone (PVP-N2O4) . Synthesis 2003 , 1591 .
  • Iranpoor , N. ; Firouzabadi , H. ; Pourali , A.-R. Dinitrogen tetroxide–impregnated charcoal (N2O4/charcoal): Selective nitrosation of amines, amides, ureas, and thiols . Synth.Commun. 2005 , 35 , 1517 .
  • Fanning , J. C. ; Keefer , L. K. ; Larry , K. Rapid formation of a potent nitrosating agent by solvolysis of ionic nitrite in dichloromethane . J. Chem. Soc., Chem. Commun. 1987 , 955 .
  • Demir , A. S. ; Mahasneh , A. S. ; Aksoy , H. ; Gercek , Z. The mild N-nitrosation of secondary amines with trichloro nitromethane . Synth. Commun. 1992 , 22 , 2607 .
  • Kang , Y. ; Zyryanov , G. V. ; Rudkevich , D. M. Towards supramolecular fixation of NOX gases: Encapsulated reagents for nitrosation . Chem. Eur. J. 2005 , 11 , 1924 .
  • Zolfigol , M. A. Efficient and chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions with sodium nitrite and oxalic acid two hydrate. Synth. Commun. 1999, 29, 905.
  • Zolfigol , M. A. ; Ghorbani-Choghamarani , A. ; Hazarkhani , H. Trichloroisocyanuric acid/NaNO2 as a novel heterogeneous system for the N-nitrosation of N,N-dialkylamines under mild conditions . Synlett 2002 , 1002 .

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