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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 8
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Original Articles

A General Synthesis of 2-Phenylselenenylenones. The Reaction of Unsaturated Ketones with a Phenylselenenyl Chloride/Pyridine Complex

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Pages 697-703 | Received 23 Apr 1979, Published online: 05 Dec 2006

References

  • Clive , D. L. J. 1978 . Tetrahedron , 34 : 1049 For a detailed outline of the scope and limitations of selen-oxide eliminations, see
  • Reich , H. J. 1979 . Accts. Chem. Res. , 12 : 22
  • Reich , H. J. , Renga , J. M. and Reich , I. L. 1974 . J. Org. Chem. , 39 : 2133
  • Reich , H. J. and Renga , J. M. 1975 . J. Org. Chem. , 40 : 3313
  • Reich , H. J. and Shah , S. K. 1977 . J. Amer. Chem. Soc. , 99 : 263
  • Reich , H. J. , Renga , J. M. and Reich , I. L. 1975 . J. Amer. Chem. Soc. , 97 : 5434
  • A number of acyclic 2-phenylselenenylenones have been prepared via propargyl selenoxide rearrangements (ref. 2c). This methodology is, of course, not applicable in the preparation of cyclic 2-phenylselenenylenones
  • In large scale reaction cooling in an ice bath may be necessary
  • Apparently in progesterone, 9, enolization of the 20-ketone is totally suppressed by pyridine, such that none of the 17- or 21-phenylselenenyl derivatives are produced (see ref. 6)
  • Sharpless , K. B. , Lauer , R. F. and Teranishi , A. Y. 1973 . J. Amer. Chem. Soc. , 95 : 6137
  • Liotta , D. and Zima , G. 1978 . Tetrahedron Lett. , : 4977 A Markovnikov addition of PhSeCl is expected. See
  • Corey , E. J. and Fraenkel , G. 1953 . J. Amer. Chem. Soc. , 75 : 1168 For an example involving pyridine in a Michael addition, see
  • Liotta , D. , Paty , P. B. , Johnston , J. and Zima , G. 1978 . Tetrahedron Lett. , : 5091 For a recent example involving the generation of an enolate via the Michael addition of a nucleophilic initiator, see
  • Besides starting material, the only observable product in this reaction is 6-phenylselenenylcyclohexenone

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