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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 1
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Original Articles

O-Silylation and Attempted O-Alkylation of Lithium Ester Enolates. The Synthesis of O-Silyl Ketene Acetals

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Pages 67-72 | Received 05 Dec 1972, Published online: 06 Dec 2006

References

  • Herbert , C. F. and House , O. 1972 . “ Chapter 9 ” . In Modern Synthetic Reactions , 2nd ed. , W. A. Benjamin, Inc. .
  • Hance , C. R. and Hauser , C. R. 1953 . J. Amer. Chem. Soc. , 75 : 994 reported only C-silyl esters from the reaction of sodium ester enolates and trimethylchlorosilane
  • Kruger , C. R. and Rochow , E. G. 1964 . J. Organometallic Chem. , 1 : 476 obtained a mixture of O-silylated (13.7%) and C-silylated (22.3%) products from the silylation of sodio ethyl acetate
  • Lutsenko , I. F. , Baukov , Y. I. , Burlachenko , G. S. and Khasapov , B. N. 1966 . J. Organometallic Chem. , 5 : 20 obtained C- and O-silylation products from the reaction of triethylsilyl iodide with the mercury salt of methyl acetate
  • Kuo , Yu-Neng , Chen , F. , Ainsworth , C. and Bloomfield , J. J. 1971 . Chem. Commun. , : 136 prepared bis-O-silyl ketene acetals from the reaction of lithio trimethylsilyl acetate and propionate with trimethylchlorosilane
  • Ireland , R. E. and Mueller , R. H. 1972 . J. Amer. Chem. Soc. , 94 : 5897 For example, have recently reported a facile Claisen rearrangement of O-trimethylsilyl-O-allyl ketene acetals
  • Rathke , M. W. and Lindert , A. 1971 . J. Amer. Chem. Soc. , 93 : 2318
  • 530 Reference 1
  • Corey , E. J. and Venkateswarlu , A. 1972 . J. Amer. Chem. Soc. , 94 : 6190
  • Storke , G. and Hudrlik , P. F. 1968 . J. Amer. Chem. Soc. , 90 : 4462
  • Tert-butyldimethylchlorosilane was prepared according to a procedure outlined by Corey6. The material is now available commercially (Willow Brook/Laboratories, Inc.)

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