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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 2
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Original Articles

Facile Aromatic Finkelstein Iodination (AFI) Reaction in 1,3-Dimethyl-2-imidazolidinone (DMI)

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Pages 170-175 | Received 12 May 2010, Published online: 14 Sep 2011

REFERENCES

  • Smith , M. B. ; March , J. March's Advanced Organic Chemistry, Reactions, Mechanisms, and Structure, , 6th ed. ; John Wiley & Sons : Hoboken , NJ , 2007 ; (a) pp. 27–31; (b) pp. 703–704; (c) p. 884, and (d) pp. 501–508 .
  • Kürti , L. ; Czakó , B. Strategic Applications of Named Reactions in Organic Synthesis ; Elsevier : Amsterdam , 2005 ; (a) Wurtz: pp. 498–499; (b) Ullmann: pp. 466–467; (c) Suzuki–Miyaura: pp. 448–449; (d) Stille–Kelly: pp. 440–441; (e) Heck: pp. 196–197; (f) Negishi: pp. 310–311; (g) Nozaki–Hiyama–Kishi: pp. 318–319; (h) Buchwald–Hartwig: pp. 70–71; (i) Sonogashira: pp. 424–425; (j) Castero–Stephens: pp. 78–79; (k) Larock: pp. 260–261; and (l) Sandmeyer: pp. 394–395 .
  • Suzuki , H. ; Kondo , A. ; Inouye , M. ; Ogawa , T. An alternative synthetic method for polycyclic aromatic iodides . Synthesis 1986 , 121 .
  • Suzuki , H. ; Kondo , A. ; Ogawa , T. Preparation of aromatic iodides from bromides via the reverse halogen exchange . Chem. Lett. 1985 , 411 .
  • Klapars , A. ; Buchwald , S. L. Copper-catalyzed halogen exchange in aryl halides: An aromatic Finkelstein reaction . J. Am. Chem. Soc. 2002 , 124 , 14844 .
  • Sheppard , T. D. Metal-catalyzed halogen exchange reactions of aryl halides . Org. Biomol. Chem. 2009 , 7 , 1043 .
  • Bacon , R. G. R. ; Hill , H. A. O. Metal ions and complexes in organic reactions, part I: Substitution reactions between aryl halides and cuprous salts in organic solvents . J. Chem. Soc. 1964 , 1097 .
  • Cornacchio , A. L. P. ; Price , J. T. ; Jennings , M. C. ; McDonald , R. ; Staroverov , V. N. ; Jones , N. D. Meta-substituted thienyl benzenes: A comparative synthetic, structural, and computational study . J. Org. Chem. 2009 , 74 , 530 , and references therein .
  • Godt , A. ; Franzen , C. ; Veit , S. ; Enkelmann , V. ; Pannier , M. ; Jeschke , G. EPR probes with well-defined, long distances between two or three unpaired electrons . J. Org. Chem. 2000 , 65 , 7575 .
  • Rosenfarb , J. ; Huffman , Jr. , H. L. ; Caruso , J. A. Dielectric constants, viscosities, and related physical properties of several substituted liquid ureas at various temperatures . J. Chem. Eng. Data 1976 , 21 , 150 .
  • Gutmann , V. The Donor–Acceptor Approach to Molecular Interactions ; Plenum : New York , 1978 ; chapter 2 .
  • Koshino , N. ; Harada , M. ; Nogami , M. ; Morita , Y. ; Kikuchi , Y. A structural study on uranyl(VI) nitrate complexes with cyclic amides: N-n-Butyl-2-pyrrolidone, N-cyclohexylmethyl-2-pyrrolidone, and 1,3-dimethyl-2-imidazolidone . Inorg. Chem. Acta 2005 , 358 , 1857 .
  • Burgess , J. Ions in Solution: Basic Principles of Chemical Interactions, , 2nd ed. ; Horwood : Chichester , 2000 ; chapter 4 .
  • Gibson , S. E. ; Mainolfi , N. ; Kalindjian , S. B. ; Wright , P. T. ; White , A. J. P. A new class of non-racemic chiral macrocycles: A conformational and synthetic study . Chem. Eur. J. 2005 , 11 , 69 .

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