scholarly journals Alkyl and Aryl Derivatives of the Alkali Metals: Strong Bases and Reactive Nucleophiles. 2. Wilhelm Schlenk’s Organoalkali-Metal Chemistry. The Metal Displacement and the Transmetalation Reactions. Metalation of Weakly Acidic Hydrocarbons. Superbases

2009 ◽  
Vol 28 (1) ◽  
pp. 2-33 ◽  
Author(s):  
Dietmar Seyferth
Author(s):  
N. S. Nametkin ◽  
V. M. Vdovin ◽  
V. A. Poletaev ◽  
N. N. Alekhin ◽  
M. B. Sergeeva

2015 ◽  
Vol 85 (7) ◽  
pp. 1791-1792
Author(s):  
N. V. Davletshina ◽  
S. A. Koshkin ◽  
A. R. Garifzyanov ◽  
R. R. Davletshin ◽  
M. A. Filimonova ◽  
...  

1960 ◽  
Vol 38 (12) ◽  
pp. 2450-2456 ◽  
Author(s):  
G. W. H. Scherf ◽  
R. K. Brown

In the solvents 1,2-dimethoxyethane (DME), 1,2-diethoxyethane (DEE), tetrahydrofuran (THF), and dioxane, potassium reacts much more readily with fluorene than does sodium or lithium. Lithium is generally more reactive than is sodium. The order of effectiveness of the ethers is DME > DEE ≈ THF > dioxane. Although practically no reaction of these metals with fluorene occurs in toluene, the addition of small amounts of these ethers to toluene does accelerate such reaction. All three organometallic compounds are soluble in refluxing and cold (22°) DME, THF, and DEE except the 9-fluorenyllithium, which precipitates largely from cold DEE. The results are explained in terms of the relative electropositivities of the metals, their size, and the structure of the ethers. It is suggested that these ethers actually participate in the formation of the organometallic compound from the metal.Sodamide and lithium amide react as readily as or more readily than the metals with fluorene in DME to produce the organometallic compounds.Diphenylmethane and triphenylmethane react reasonably well with potassium in DME, but too slowly with lithium and sodium to be useful.


It is more than 30 years since the foundation of organo-transition metal chemistry and its useful applications. The names of Nobel Laureates E. O. Fischer and G. Wilkinson, K .Ziegler and G. Natta are associated with the earliest years of the development of this field. Indeed, the early chemistry of hydrocarbon derivatives of transition metals was largely developed by inorganic chemists whose primary interest focused on the transition metal chemistry rather than on transformations of organic compounds. Apart from a few, academic organic chemists were rather slow to appreciate the potential of organo-transition metal compounds as synthetic intermediates. What were the reasons for this delay? It was perhaps because in the early days of the development of organo-transition metal chemistry it was difficult to perceive pattern and order in the abundant complexity of new structural types and reactivities. Indeed, in the early days the fragmentary knowledge and understanding mitigated against much pretence of deeply argued strategies for research. Also, new techniques such as the need to work under an inert atmosphere with a vacuum/nitrogen line were unfamiliar to organic chemists


1969 ◽  
Vol 19 (2) ◽  
pp. 327-337 ◽  
Author(s):  
R.B. King ◽  
K.H. Pannell ◽  
C.R. Bennett ◽  
M. Isahq

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