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New Properties of Reagents by Complexation of Carbanions on Transition-Metals: Which Metal is in Each Case the Most Favorable One?

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Organometallics in Organic Synthesis 2

Abstract

The transmetallation of carbanionid derivatives of Li, Mg or Zn by treating with transition-metal halides is the most important method for the preparation of transition-metal alkyls. This method seems to have no limitations with regard to the kind of the transition-metal and allows also the synthesis of very thermolabile alkyl derivatives, because the transmetallation occurs normally even below -60°C at a high rate. In those reactions the carbanionic residue is coordinated to a transition-metal according to Scheme 1, causing serious changes in the properties of the alkyl derivatives. The changes, stated in scheme 1, have proved to be useful in organic synthesis.

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References

  1. Übergangsmetallaktivierte organische Verbindungen, Part 29 - Part 28: Kauffmann T in “Advances in Metal Carbene Chemistry”, Reidel, in press

    Google Scholar 

  2. Whitesides GM, Stedronsky ER, Casey CP, San Filippo Jr J (1970) J Am Chem Soc 92: 1426

    Article  CAS  Google Scholar 

  3. Kauffmann T (1974) Angew Chem 86:321; Angew Chem Int Ed Engl 13:291; ibid, 91:1; Angew Chem Int Ed Engl 18:1 and later publications in Chem Ber

    Article  CAS  Google Scholar 

  4. Jackisch J, Legier J, Kauffmann T (1982) Chem Ber 115: 659

    Article  CAS  Google Scholar 

  5. Kharasch M, Tawney PO (1941) J Am Chem Soc 63: 2308

    Article  CAS  Google Scholar 

  6. a: Posner GH, Whitten CE, McFarland PE (1972) J Am Chem Soc 94: 5106 b: Posner GH in “An Introduction to Synthesis Using Organocopper Reagents”, Wiley & Sons, New York 1980

    Article  CAS  Google Scholar 

  7. Cahiez G, Normant JF, Tetrahedron Lett 1977:3383; Normant JF, Cahiez G in “Modern Synthetic Methods 1983”, S 173; Editor: Scheffold R, Salle-Verlag, Frankfurt/M 1983

    Google Scholar 

  8. Reetz MT, “Organotitanium Reagents in Organic Synthesis”, Springer Verlag, Berlin 1986

    Book  Google Scholar 

  9. Seebach D, Weidmann B, Widler L in “Modern Synthetic Methods 1983”, S 217; Editor: Scheffold R, Salle-Verlag, Frankfurt/M 1983

    Google Scholar 

  10. Kauffmann T, Hamsen A, Beirich C (1982) Angew Chem 94:145; Angew Chem Int Ed Engl 21: 144

    Article  Google Scholar 

  11. Kauffmann T, Antfang E, Ennen B, Klas N, Tetrahedron Lett 1982: 2301

    Google Scholar 

  12. Kauffmann T, Pahde C, Wingbermühle D (1985) Tetrahedron Lett 26: 4059

    Article  CAS  Google Scholar 

  13. Kauffmann T, Pahde C, Tannert A, Wingbermühle D (1985) Tetrahedron Lett 26: 4063

    Article  CAS  Google Scholar 

  14. Kauffmann T and co-workers, unpublished

    Google Scholar 

  15. D’Ans-Lax, Taschenbuch für Chemiker und Physiker, 3 Ed, Vol 1, Springer Verlag, Berlin 1967

    Google Scholar 

  16. Nishimura K, Kuribayashi H, Yamamoto A, Ikeda S (1972) J Organomet Chem 37:317; Thiele KH, Zdunneck P, Baumgart D (1970) Z Anorg Allg Chem 378: 62

    Article  CAS  Google Scholar 

  17. a: Abel T, Diplomarbeit Universität Münster, 1985; b: Kauffmann T, Abel T, Schreer M, Wingbermühle D (1987) Tetrahedron 43: 2021

    Google Scholar 

  18. a: Loc cit 8, page 81; b: Reetz MT, Kyung SH, Hüllmann M (1986) Tetrahedron 42: 2931

    Google Scholar 

  19. Wilkins JD (1974) J Organomet Chem 80: 357

    Article  CAS  Google Scholar 

  20. Kauffmann T, Abel T, Schreer M (1988) Angew Chem 100:1006; Angew Chem Int Ed Engl 27: 944

    Article  CAS  Google Scholar 

  21. a: Reetz MT, Wenderoth B (1982) Tetrahedron Lett 23:5259; b: Reetz MT, Wenderoth B, Peter R, J Chem Soc Chem Commun 1983: 406

    Google Scholar 

  22. Kauffmann T, König R, Pahde C, Tannert A (1981) Tetrahedron Lett 22: 5031

    Article  CAS  Google Scholar 

  23. Reetz MT, Westermann J, Steinbach R, Wenderoth B, Peter R, Ostarek R, Maus S (1985) Chem Ber 118: 1421

    Article  CAS  Google Scholar 

  24. Reetz MT, Steinbach R, Wenderoth B, Westermann J, Chem Ind 1981: 541

    Google Scholar 

  25. Kauffmann T, Schwartze P (1986) Chem Ber 119: 2150

    Article  CAS  Google Scholar 

  26. Synthesis and synthetic application of Ph2AsCH2Li: Kauffmann T, Altepeter B, Klas N, Kriegesmann R (1985) Chem Ber 118: 2353

    Google Scholar 

  27. Okude Y, Hirano S, Hiyama T, Nozaki H (1977) J Am Chem Soc 99: 3179

    Article  CAS  Google Scholar 

  28. Posner GH, Whitten CE, Sterling JJ (1973) J Am Chem Soc 95: 7788

    Article  CAS  Google Scholar 

  29. Cahiez G, Masuda A, Bernard D, Normant JF Tetrahedron Lett 1976: 3155

    Google Scholar 

  30. Hegedus LS, Kendall PM, Lo SM, Sheats JR (1975) J Am Chem Soc 97: 5448

    Article  CAS  Google Scholar 

  31. Kauffmann T, Abel T, Beirich C, Kieper G, Pahde C, Schreer M, Toliopoulos E, Wieschollek R (1986) Tetrahedron Lett 27: 5355

    Article  CAS  Google Scholar 

  32. Kauffmann T, Abeln R, Wingbermühle D (1984) Angew Chem 96:724; Angew Chem Int Ed Engl 23: 729

    Google Scholar 

  33. Reetz MT (1982) Top Curr Chem 106: 1

    CAS  Google Scholar 

  34. Kauffmann T, Möller T, Rennefeld H, Welke S, Wieschollek R (1985) Angew Chem 97:351, Angew Chem Int Ed Engl 24: 348

    Google Scholar 

  35. Kauffmann T, Abel K, Bonrath W, Kolb M, Möller T, Pahde C, Raedeker S, Robert M, Wensing M, Wichmann B (1986) Tetrahedron Lett 27: 5351

    Article  CAS  Google Scholar 

  36. Reetz MT (1984) Angew Chem 96:542; Angew Chem Int Ed Engl 23: 556

    Google Scholar 

  37. Term “Chelator”: Lahiri GK, Bhattacharya S, Ghosh BK, Chakravorty A (1987) Inorg Chem 26:4324

    Google Scholar 

  38. The term “grouping selectivity”, proposed three years ago [34], has been substituted by the term “cheleselectivity” 1 because “grouping selectivity” is to be confused easily with “functional group selectivity” or “chemoselectivity”

    Google Scholar 

  39. Reetz MT, Maus S (1987), Tetrahedron 43: 101

    Article  CAS  Google Scholar 

  40. Kauffmann T, Fobker R, Wensing M (1988) Angew Chem 100:1005; Angew Chem Int Ed Engl 27: 943

    Google Scholar 

  41. Kauffmann T, Ennen B, Sander J, Wieschollek R (1983) Angew Chem 95:237; Angew Chem Int Ed Engl 22: 244

    Google Scholar 

  42. Kauffmann T, Abeln R, Welke S, Wingbermühle D (1986) Angew Chem 98:927; Angew Chem Int Ed Engl 25: 909

    Google Scholar 

  43. Kauffmann T, Kieper G (1984) Angew Chem 96:502; Angew Chem Int Ed Engl 23:532

    Google Scholar 

  44. Kauffmann T, Fiegenbaum P, Wieschollek R (1984) Angew Chem 96: 500; Angew Chem Int Ed Engl 23: 531

    Google Scholar 

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Author information

Authors and Affiliations

  1. Organisch-Chemisches Institut der Universität Münster, Corrensstr. 40, D-4400, Münster, Federal Republic of Germany

    Thomas Kauffmann

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  1. Thomas Kauffmann
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Editors and Affiliations

  1. Institut für Anorganische Chemie der Universität Würzburg, Am Hubland, D-8700, Würzburg, Germany

    Helmut Werner

  2. Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-8700, Würzburg, Germany

    Gerhard Erker

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© 1989 Springer-Verlag Berlin Heidelberg

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Kauffmann, T. (1989). New Properties of Reagents by Complexation of Carbanions on Transition-Metals: Which Metal is in Each Case the Most Favorable One?. In: Werner, H., Erker, G. (eds) Organometallics in Organic Synthesis 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-74269-9_10

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  • DOI: https://doi.org/10.1007/978-3-642-74269-9_10

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-50531-0

  • Online ISBN: 978-3-642-74269-9

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