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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 2
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Original Articles

Efficient Bromination of Alkenes and Alkynes Using Potassium Bromide and Diacetoxy Iodobenzene

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Pages 220-227 | Received 22 Dec 2007, Published online: 22 Dec 2008

REFERENCES

  • House , H. O. Modern Synthetic Reactions, , 2nd ed.; W. A. Benjamin Inc ., Menlo Park , CA , 1972 ; p. 422 .
  • Ranu , B. C. ; Guchhait , S. K. ; Sarkar , A. Stereoselective debromination of aryl-substituted vic-dibromide with indium metal . Chem. Commun. 1998 , 2113 .
  • Rieke , R. D. ; Sell , M. S. In Handbook of Grignard Reagents ; G. S. Silverman and P. E. M. Rakita (Eds.); Dekker : New York , 1996 ; Chap. 26, p. 527.
  • Fieser , L. F. ; Fieser , M. Reagents for Organic Synyhesis ; Wiley : New York , 1967 : Vol. 1 , p. 967 .
  • Berthelot , J. ; Benammar , Y. ; Lange , C. A mild and efficient sonochemical bromination of alkenes using tetrabutylammonium tribromide . Tetrahedron Lett. 1991 , 32 , 4135 .
  • Hazra , G. ; Chordia , M. D. ; Bahule , B. B. ; Pore , V. S. ; Basu , S. Manganese-mediated novel dibromination of olefins with tetradecyltrimethylammonium permanganate and trimethylbromosilane . J. Chem. Soc., Perkin Trans. 1 , 1994 , 1667 .
  • Barhate , N. B. ; Gaajare , A. S. ; Wakharkar , R. D. ; Bedekar , A. V. Simple and practical halogenation of arenes, alkenes, and alkynes with hydrohalic acid/H2O2 (or TBHP) . Tetrahedron 1999 , 55 , 11127 .
  • Rodebaugh , R. ; Dahenham , J. S. ; Fraser-Reid , B. ; Snyder , J. P. Bromination of alkenyl glycosides with copper(II) bromide and lithium bromide: Synthesis, mechanism, and DFT calculations . J. Org. Chem , 1999 , 64 , 1758 .
  • Nair , V. ; Panicker , S. B. ; Augustine A.: George , T. G. ; Thomas , S. ; Vairamani , M. An efficient bromination of alkenes using cerium(IV) ammonium nitrate (CAN) and potassium bromide . Tetrahedron 2001 , 57 , 7417 .
  • Moriuchi , T. ; Yamaguchi , M. ; Kikushimia , K. ; Hirao , T. An efficient vanadium-catalyzed bromination reaction . Tetrahedron Lett. 2007 , 48 , 2667 .
  • Das , B. ; Venkateswarlu , K. ; Mahender , G. ; Mahender , I. A simple and efficient method for α -bromination of carbonyl compounds using N-bromosuccinimide in the presence of silica-supported sodium hydrogen sulfate as a heterogeneous catalyst . Tetrahedron Lett. 2005 , 46 , 3041 .
  • Das , B. ; Ramu , R. ; Ravikanth , B. ; Reddy , K. R. Regioselective ring-opening of aziridines with potassium thiocyanate and thiols using sulfated zirconia as a heterogeneous recyclable catalyst . Tetrahedron Lett. 2006 , 47 , 779 .
  • Das , B. ; Venkateswarlu , K. ; Krishnaiah , M. ; Synthesis of β-chlorohydrins in water Helv. Chim. Acta 2007 , 90 , 149 .
  • Varvoglis , A. Hypervalent Iodine in Organic Synythesis ; Academic : New York , 1997 .
  • Wirth , T. Hypervalent iodine chemistry: Modern development in organic synthesis , In Topics in Current Chemistry ; Springer : Berlin , 2003 : p. 224 .
  • Das , B. ; Holla , H. ; Mahender , G. ; Banrjee , J. ; Reddy , M. R. Hypervalent iodine-mediated interaction of aldoximes with activated alkenes including Baylis–Hillman adducts: A new and efficient method for the preparation of nitrile oxides from aldoximes . Tetrahedron Lett. 2004 , 45 , 7347 .
  • Part 158 in the series, “Studies on Novel Synthetic Methodologies.”

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