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

Preparation of 1-Alkynyl (Trimethyl) Silanes from Trimethylsilylpropargyl Phenyl Ether and Organoboranes

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Pages 809-817 | Received 01 Jun 1979, Published online: 05 Dec 2006

References

  • Cragg , C. M. L. 1973 . “Organoboranes in Organic Synthesis,” , New York : Marcel Dekker . For recent books and reviews, see
  • Brown , H. C. 1975 . “Organic Syntheses via Boranes,” , New York : John Wiley & Sons .
  • Negishi , E. 1976 . J. Organometal. Chem. , 108 : 281
  • Negishi , E. 1976 . “New Applications of Organometallic Reagents in Organic Synthesis,” , Edited by: Seyferth , D. 93 Amsterdam : Elsevier .
  • Weill-Raynal , J. 1976 . Synthesis , : 633
  • Avasthi , K. , Devaprabhakara , D. and Suzuki , A. 1979 . “Organometallic Chemistry Reviews,” , Edited by: Seyferth , D. 1 Amsterdam : Elsevier .
  • Leung , T. and Zweifel , G. 1974 . J. Amer. Chem. Soc. , 96 : 5620
  • Midland , M. M. 1977 . J. Org. Chem. , 42 : 2650
  • Zweifel , G. , Backlund , S. J. and Leung , T. 1978 . J. Amer. Chem. Soc. , 100 : 5561
  • Hudrlik , P. F. 127 For reviews, see, in ref. Id
  • Washburne , S. S. 1976 . J. Organometal. Chem. , 123 : 1
  • Hara , S. , Kishimura , K. and Suzuki , A. 1978 . Tetrahedron Lett. , : 2891
  • Trimethylsilylpropargyl phenyl ether (1) was recovered in a 85% yield after protonolysis of the carbanion formed under the same conditions (-78oC, 30 min). The IR spectrum of the recovered 1 showed no allenic absorption, indicating that the structure of the generated carbanion is propargylic but not allenic
  • Landor , S. R. , Patel , A. N. , Whiter , P. F. and Graves , P. M. 1966 . J. Chem. Soc. (C) , : 1223
  • Zweifel , G. and Backlund , S. J. 1977 . J. Amer. Chem. Soc. , 99 : 3184
  • Prepared by the reaction of 3-phenoxy-1-propyne with trimethylsilyl chloride in the presence of butyllithium

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