Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 10
682
Views
111
CrossRef citations to date
0
Altmetric
Original Articles

Facile Conversion of Primary and Secondary Alcohols to Alkyl Iodides

&
Pages 1473-1479 | Received 27 Feb 1990, Published online: 24 Oct 2006

References

  • Giese , B. 1986 . “ Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds ” . Oxford : Pergamon Press .
  • Garegg , P. J. and Samuelsson , B. 1980 . J. Chem. Soc., Perkin Trans. , I : 2866
  • Garegg , P. J. , Johansson , R. , Ortega , C. and Samuelsson , G. 1982 . J. Chem. Soc., Perkin Trans. , I : 681
  • Classon , B. and Liu , Z. 1988 . J. Org. Chem. , 53 : 6126
  • Munyemana , F. , Frisque-Hesbain , A.-M. , Devos , A. and Ghosez , L. 1989 . Tetrahedron Lett. , 30 : 3077
  • Jung , M. E. and Ornstein , P. L. 1977 . Tetrahedron Lett. , 2659
  • Imamoto , T. , Matsumoto , T. , Kusumoto , T. and Yokoyama , M. 1983 . Synthesis , 460
  • Lange , G. L. , Decicco , C. P. , Willson , J. and Strickland , L. A. 1989 . J. Org. Chem. , 54 : 1805 For a solvolysis study on the strained iodide 2c see
  • Garegg , P. J. , Regberg , T. , Stawinski , J. and Stromberg , R. 1987 . J. Chem. Soc., Perkin Trans. , I : 271
  • The conversion was unsuccessful even with two equivalents of the reagents, with added (n-Bu)4N+Iθ, and heating to reflux
  • Yu , D. and d'Alarcao , M. 1989 . J. Org. Chem. , 54 : 3240
  • Keinan , E. and Perez , D. 1987 . J. Org. Chem. , 52 : 4816
  • The values calculated for the optical purity of (-)-2-iodooctane in ref. (6) are in error
  • Filippo , J. S. and Romano , L. J. 1975 . J. Org. Chem. , 40 : 1514
  • Hayes , R. K. and Holden , M. 1982 . Aust. J. Chem. , 35 : 517
  • Mori , K. , Masuda , S. and Suguro , T. 1981 . Tetrahedron , 37 : 1329
  • Hoffmann , H. M. R. 1964 . J. Chem. Soc. , 1249
  • Oshikawa , T. and Yamashita , M. 1984 . Bull. Chem. Soc. Jpn. , 57 : 2675
  • The imidazole should be in solution before the iodine is added. A fine white precipitate of imidazole-HI forms after this addition .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.