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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 12, 1982 - Issue 13
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Original Articles

Simple Preparation of 1-Bromo-1-Trimethylsilyl-1(Z), 4-pentadiene and its Use as 4-Pentenoyl Anion Equivalent

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Pages 1027-1037 | Published online: 06 Dec 2006

References

  • Colvin , E. W. 1981 . “Silicon in Organic Synthesis” , London : Butterworths .
  • Zweifel , Z. and Lewis , W. 1978 . J. Org. Chem. , 43 : 2739 Synthesis and reactions of α-haloalkenylsilanes; and references cited therein.
  • Miller , R. B. and McGarvey , G. 1979 . J. Org. Chem. , 44 : 4623
  • On , H. P. , Lewis , W. and Zweifel , G. 1981 . Synthesis , : 999
  • Yamaguchi , R. , Kawasaki , H. , Yoshitome , T. and Kawanisi , M. submitted for publication
  • Seebach , D. 1979 . Angew. Chem. Int. Ed. Engl. , 18 : 239 For polarity Umpolung
  • Stork , G. and Colvin , E. 1971 . J. Amer. Chem. Soc. , 93 : 2080
  • Stork , G. and Jung , M. E. 1974 . J. Amer. Chem. Soc. , 96 : 3682
  • Stork , G. , Jung , M. E. , Colvin , E. W. and Noel , Y. 1974 . J. Amer. Chem. Soc. , 96 : 3684
  • Boeckman , R. K. Jr. and Bruza , K. J. 1979 . J. Org. Chem. , 44 : 4781 For use of α-metallated vinylsilanes as acyl anion equivalents
  • Gröbel , B.-T. and Seebach , D. 1977 . Chem. Ber. , 110 : 867
  • Huynh , C. and Linstrumelle , G. 1979 . Tetrahedron Lett. , : 1073
  • Luche , J.-L. and Damiano , J.-C. 1980 . J. Amer. Chem. Soc. , 104 : 7926 The reaction could not proceed without ultrasound. For ultrasound assisted preparation of organometallics
  • Posner , G. H. 1980 . “An Introduction to Synthesis Using Organocopper Reagents” , New York : John Wiley & Sons . See also ref. 2c
  • Utimoto , K. , Kitai , M. and Nozaki , H. 1975 . Tetrahedron Lett. , : 2825 A treatment of (E)-5a with HI in PhH gave 1,4(Z)-undecadiene. For stereoselective desilylation of alkenylsilane
  • Sakurai , H. , Hayashi , N. and Kumada , M. 1969 . J. Organometal. Chem. , 18 : 351 Rate of epoxidation of vinylsilane is faster than that of terminal olefin
  • In the absence of trimethylsilyl chloride, the yield was lower.
  • Tsuji , J. , Shimizu , I. and Yamamoto , K. 1976 . Tetrahedron Lett. , : 2975
  • Indeed, λ, δ-unsaturated ketones (5a, 5b, 5c) were converted to 1,4-dicarbonyl compounds by palladium-catalyzed oxidation 11) and then to cyclopentenones by base-promoted cyclization.
  • Ho , T.-L. 1982 . Synth. Commun. , 12 : 53

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