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A New Facile One-Pot Method for Preparation of 1,1-bis(silyl)alkene Via Imine Precursor

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Abstract

Aniline reacts with variety of aryl aldehydes in ethanol to afford the corresponding imines. The reaction of imines with tris(dimethylsilyl)methyl lithium, (HMe2Si)3CLi, in THF at − 10°C gives 1,1-bis(silyl)-1-alkenes derivatives bearing Si-H functional and reactive groups.

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References

  1. Colvin E (1988) Silicon reagents in organic synthesis. Academic Press, London

    Google Scholar 

  2. Patai S, Rappoport Z (1988) The chemistry of organosilicon compounds. Wiley, Chichester, England

    Google Scholar 

  3. Inoue A, Kondo J, Shinokubo H, Oshima K (2002) Chem Commun 2:114

    Article  Google Scholar 

  4. Inoue A, Kondo J, Shinokubo H, Oshima K (2001) J Am Chem Soc 123:11109

    Article  CAS  Google Scholar 

  5. Hodgson D, Comina P, Drew M (1997) J Chem Soc Perkin Trans 1:2279

    Article  Google Scholar 

  6. Hodgson D, Comina P (1996) J Chem Commun 6:755

    Article  Google Scholar 

  7. Jankowski P, Pleśniak K (2003) J Org Lett 5:2789

    Article  CAS  Google Scholar 

  8. Gröbel B, Seebach D (1977) Chem Ber 110:852

    Article  Google Scholar 

  9. Fleming I, Floyd D (1981) J Chem Soc Perkin Trans 1:969

    Article  Google Scholar 

  10. Fleming I, Ghosh U (1994) J Chem Soc Perkin Trans 1:257

    Article  Google Scholar 

  11. Narasaka K, Saito N, Hayashi Y, Ichida H (1990) Chem Lett 1411

  12. Negishi E, Boardman L, Sawada H, Bagheri V (1988) J Am Chem Soc 110:5383

    Article  CAS  Google Scholar 

  13. Flann C, Malone T, Overman L (1987) J Am Chem Soc 109:6097

    Article  CAS  Google Scholar 

  14. Blumenkopf T, Overman L (1986) Chem Rev 86:857

    Article  CAS  Google Scholar 

  15. Inoue A, Kondo J, Shinokubo H, Oshima K (2001) Chem Lett 10:956

    Article  Google Scholar 

  16. Kondo J, Inoue A, Shinokubo H, Oshima K (2002) Tetrahedron Lett 43:2399

    Article  CAS  Google Scholar 

  17. Safa K, Hassanpour A, Tofangdarzadeh S (2008) J Organomet Chem 693:3622

    Article  CAS  Google Scholar 

  18. Safa K, Hassanpour A, Tofangdarzadeh S (2009) Synthetic communications 9:1601

    Article  Google Scholar 

  19. International union of pure and applied chemistry. “imines”. Compendium of Chemical Terminology Internet edition

  20. March Jerry (1985) Advanced Organic Chemistry reactions, mechanisms and structure, 3rd edn. John Wiley & Sons, New York: ISBN 0-471-85472-7

    Google Scholar 

  21. Fletcher, Dermer, Fox (1974) Nomenclature of Organic Compounds

  22. Patai S (1970) The chemistry of the carbon–nitrogen double bond. Wiley, London

    Book  Google Scholar 

  23. Patai S (1968) The chemistry of the amino group. Wiley, London

    Google Scholar 

  24. Patai S (1966) The chemistry of the carbonyl group. Wiley, London

    Google Scholar 

  25. Layer R (1963) Chem Rev 63:489

    Article  CAS  Google Scholar 

  26. Goering B (1955) Ph.D. Dissertation, Cornell University

  27. Otto S (2006) Chem Rev 106:3652

    Article  Google Scholar 

  28. Meyer C, Joiner C, Stoddart J (1705) Chem Soc Rev 36:1705

    Article  Google Scholar 

  29. Rowan S, Cantrill S, Cousins G (2002) Angew Chem 114:938

    Article  Google Scholar 

  30. Storm O, Lüning U (2002) Chem Eur J 8:793

    Article  CAS  Google Scholar 

  31. Hawrelak E, Ladipo F, Sata D (1999) Organometallics 18:1804

    Article  CAS  Google Scholar 

  32. Shibata I, Kawakami T, Tanizawa D (1998) J Org Chem 63:383

    Article  CAS  Google Scholar 

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Correspondence to Yones Mosaei Oskoei.

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Oskoei, Y.M., Mousavi-azar, A., Madram, A. et al. A New Facile One-Pot Method for Preparation of 1,1-bis(silyl)alkene Via Imine Precursor. Silicon 4, 251–257 (2012). https://doi.org/10.1007/s12633-012-9128-9

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  • DOI: https://doi.org/10.1007/s12633-012-9128-9

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