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.
Keywords
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Übergangsmetallaktivierte organische Verbindungen, Part 29 - Part 28: Kauffmann T in “Advances in Metal Carbene Chemistry”, Reidel, in press
Whitesides GM, Stedronsky ER, Casey CP, San Filippo Jr J (1970) J Am Chem Soc 92: 1426
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
Jackisch J, Legier J, Kauffmann T (1982) Chem Ber 115: 659
Kharasch M, Tawney PO (1941) J Am Chem Soc 63: 2308
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
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
Reetz MT, “Organotitanium Reagents in Organic Synthesis”, Springer Verlag, Berlin 1986
Seebach D, Weidmann B, Widler L in “Modern Synthetic Methods 1983”, S 217; Editor: Scheffold R, Salle-Verlag, Frankfurt/M 1983
Kauffmann T, Hamsen A, Beirich C (1982) Angew Chem 94:145; Angew Chem Int Ed Engl 21: 144
Kauffmann T, Antfang E, Ennen B, Klas N, Tetrahedron Lett 1982: 2301
Kauffmann T, Pahde C, Wingbermühle D (1985) Tetrahedron Lett 26: 4059
Kauffmann T, Pahde C, Tannert A, Wingbermühle D (1985) Tetrahedron Lett 26: 4063
Kauffmann T and co-workers, unpublished
D’Ans-Lax, Taschenbuch für Chemiker und Physiker, 3 Ed, Vol 1, Springer Verlag, Berlin 1967
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
a: Abel T, Diplomarbeit Universität Münster, 1985; b: Kauffmann T, Abel T, Schreer M, Wingbermühle D (1987) Tetrahedron 43: 2021
a: Loc cit 8, page 81; b: Reetz MT, Kyung SH, Hüllmann M (1986) Tetrahedron 42: 2931
Wilkins JD (1974) J Organomet Chem 80: 357
Kauffmann T, Abel T, Schreer M (1988) Angew Chem 100:1006; Angew Chem Int Ed Engl 27: 944
a: Reetz MT, Wenderoth B (1982) Tetrahedron Lett 23:5259; b: Reetz MT, Wenderoth B, Peter R, J Chem Soc Chem Commun 1983: 406
Kauffmann T, König R, Pahde C, Tannert A (1981) Tetrahedron Lett 22: 5031
Reetz MT, Westermann J, Steinbach R, Wenderoth B, Peter R, Ostarek R, Maus S (1985) Chem Ber 118: 1421
Reetz MT, Steinbach R, Wenderoth B, Westermann J, Chem Ind 1981: 541
Kauffmann T, Schwartze P (1986) Chem Ber 119: 2150
Synthesis and synthetic application of Ph2AsCH2Li: Kauffmann T, Altepeter B, Klas N, Kriegesmann R (1985) Chem Ber 118: 2353
Okude Y, Hirano S, Hiyama T, Nozaki H (1977) J Am Chem Soc 99: 3179
Posner GH, Whitten CE, Sterling JJ (1973) J Am Chem Soc 95: 7788
Cahiez G, Masuda A, Bernard D, Normant JF Tetrahedron Lett 1976: 3155
Hegedus LS, Kendall PM, Lo SM, Sheats JR (1975) J Am Chem Soc 97: 5448
Kauffmann T, Abel T, Beirich C, Kieper G, Pahde C, Schreer M, Toliopoulos E, Wieschollek R (1986) Tetrahedron Lett 27: 5355
Kauffmann T, Abeln R, Wingbermühle D (1984) Angew Chem 96:724; Angew Chem Int Ed Engl 23: 729
Reetz MT (1982) Top Curr Chem 106: 1
Kauffmann T, Möller T, Rennefeld H, Welke S, Wieschollek R (1985) Angew Chem 97:351, Angew Chem Int Ed Engl 24: 348
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
Reetz MT (1984) Angew Chem 96:542; Angew Chem Int Ed Engl 23: 556
Term “Chelator”: Lahiri GK, Bhattacharya S, Ghosh BK, Chakravorty A (1987) Inorg Chem 26:4324
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”
Reetz MT, Maus S (1987), Tetrahedron 43: 101
Kauffmann T, Fobker R, Wensing M (1988) Angew Chem 100:1005; Angew Chem Int Ed Engl 27: 943
Kauffmann T, Ennen B, Sander J, Wieschollek R (1983) Angew Chem 95:237; Angew Chem Int Ed Engl 22: 244
Kauffmann T, Abeln R, Welke S, Wingbermühle D (1986) Angew Chem 98:927; Angew Chem Int Ed Engl 25: 909
Kauffmann T, Kieper G (1984) Angew Chem 96:502; Angew Chem Int Ed Engl 23:532
Kauffmann T, Fiegenbaum P, Wieschollek R (1984) Angew Chem 96: 500; Angew Chem Int Ed Engl 23: 531
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1989 Springer-Verlag Berlin Heidelberg
About this paper
Cite this paper
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
Download citation
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
eBook Packages: Springer Book Archive