Wiirtz reaction

The oldest method for generating a Ge—Ge bond is the Wiirtz reaction from a tri-organogermanium halide and sodium1 ... 

An important method of alkylation or arylation comparable to the Wiirtz reaction uses germanium tetraiodide31 ... 

The Wiirtz reaction can be used to incorporate some functionality in an alkyl chain bound to tin in a stannane111, e.g. by reaction of Ph3SnCH2I or (ICH2)4Sn respectively with RSNa (where RH = benzothiazole, benzoxazole, 1-methylimidazole, pyrimidine). Compounds of the type Ph3SnCH2SR or (RSCH2)4Sn were obtained. 

The reaction is similar to the Wiirtz reaction, but the distribution of the valence electrons or the charges on the separate atoms are not known with the same certainty. 

Of the synthetic reactions of the alkyl halides that with potassium cyanide, which enabled H. Kolbe to synthesise acetic acid from a methane derivative, has already been mentioned (cf. the preparations on pp. 137 and 254). Of the simpler syntheses that of Wiirtz may be mentioned here. Metallic sodium removes the halogen from two molecules and the two radicles combine. Thus, in the simplest case, ethane is formed from methyl bromide ... 

WURTZ-FITTIG-FRANKLAND REACTION. Sodium metal was used by Wiirtz as reagent for the preparation of paraffin hydrocarbons... 

Reaction VR (a) Action of Sodium on Halogen Compounds (Wiirtz, Fittig, and Freund). (A., 131, 303.)—The application of this reaction to the synthesis of paraffins by Wiirtz was of great importance to chemical theory, as it afforded strong evidence of the chain linking of carbon atoms, and enabled the structure of many hydrocarbons to be determined by their syntheses. 

Barbier-Wieland degradation Boudroux-Chichibabin synthesis Bouveault aldehyde synthesis Darzens synthesis Friedel-Crafts Reaction Gatterman-Koch reaction Grignard reaction Reformatsky reaction Saytzeff reaction Ullmann coupling reaction Wiirtz coupling reaction Wiirtz-Fittig reaction... 

In order to keep the reaction time as short as possible, a considerable excess of lithium should be used in the preparation of the lithiocycloalkenes. All chloro-cycloalkene can be added in one portion, if the reaction is carried out on a modest scale (0.3-0.5 molar), the reaction can be kept under control by changing the rate of stirring. Wiirtz coupling to C12 or C14 hydrocarbons and/or HC1 elimination (under the influence of lithiocycloalkene) do not occur. 

These simple and well-known reactions of inorganic chemistry are paralleled in organic chemistry by the Wiirtz and Fittig syntheses and the Barbier-Grignard reaction. The Wiirtz and Fittig syntheses may be formulated in most general terms as follows ... 

The Wiirtz coupling of methylphenyldichlorosilane by a molten sodium dispersion in toluene obeys the following reaction ... 

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