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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 8, 1978 - Issue 8
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Original Articles

The Reactivity of t-Butyldimethylsilyl Ethers Towards Some Stabilised Carbanions

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Pages 573-577 | Received 04 May 1978, Published online: 06 Dec 2006

References

  • Corey , E. J. and Venkateswarlu , A. 1972 . J. Am. Chem. Soc. , 94 : 6190
  • Ogilvie , K. K. and Iwacha , D. J. 1973 . Tetrahedron Letters , : 317
  • Hosoda , H. , Yamashita , K. and Nambara , T. 1975 . Chem. Ind. London , : 650
  • Dodd , G. H. , Golding , B. T. and Ioannou , P. V. 1975 . Chem. Comm. , : 249
  • Arai , I. , Park , K.-H. and Daves , G. D. Jr. 1976 . J. Organomet. Chem. , 121 : 25
  • Hase , T. unpublished work
  • Midgley , J. M. , Millership , J. S. and Whalley , W. B. 1976 . J. Chem. Soc. Perkin I , : 1384
  • All new compounds exhibited satisfactory spectral and physical properties
  • Reagent generated with LDA in THF at 0°; subsequent reaction time 8 h at 0°
  • Seebach , D. and Kolb , M. 1977 . Justus Liebigs Ann. Chem. , : 811
  • Kajikawa , A. , Morisaki , M. and Ikekawa , N. 1975 . Tetrahedron Lett. , : 4135
  • Only alkylations of 4 have been reported13; our experience is that the reaction of 4 with simple carbonyl compounds (benzaldehyde, 3-TBDMS-O-benzal-dehyde, etc.) is very unsatisfactory
  • Hertenstein , U. , Hünig , S. and Öler , M. 1976 . Synthesis , : 416
  • SiR3 = SiMe2Bu-t; all substrates were prepared by the silyl chloride/imidazole/DMF procedure 1,8
  • Isolated yields
  • Hanessian , S. and Lavallee , P. 1975 . Can. J. Chem. , 53 : 2975

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