Organolithium reagents organomercury

Halophosphines can be treated with organometaUic reagents, eg, Grignard reagents, organomercuries, and organolithiums, to produce tertiary phosphines. 

An alternative method for preparing metallocenyllithium derivatives, convertible into organosilicon compounds, is based on cleavage of organomercury compounds with organolithium reagents. It was used for the silylation of ferrocene (113, 151) ... 

Metathesis reactions continue to be extensively employed in the synthesis of organomercury compounds. While most reactions involve the use of organolithium or Grignard reagents, other organometallic compounds are sometimes used as starting materials. 

Organoboranes (such as aryl and vinyl boronic acids) have also demonstrated to be valuable reagents for the synthesis of organomercurials, particularly in the presence of functional groups that are not compatible with the more reactive organolithium or -magnesium reagents. 

The preparation of organolithiums by reaction (a) is of limited synthetic utility because the organomercurials are prepared from other organometallic reagents, most often organomagnesium halides or organolithiums. In addition, reaction (a) is slow, although ultrasonic irradiation increases the rate. 

In this section, we will discuss organometallics in which the metal is cadmium, mercury, or zinc. Grignard reagents and organolithium compounds can be converted to heavy-metal derivatives by reaction with salts of these metals. The reaction is driven forward by the tendency for formation of the ionic salt of the more electropositive metal. This reaction is well documented for organocadmium compounds and organomercurials ... 

Grignard reagents are also synthesized by addition reactions of alkynes, addition reactions of unsaturated compounds having C=S groups, reactions of cycloalkanes, reactions with organolithium compounds or organomercury compounds, etc. [4,15,27,28],... 

As shown in eqs. (5.3)-(5.7), organozinc compounds are easily prepared by the reactions of zinc compounds or zinc metal with organometallic compounds such as Grignard reagents, organoaluminum compounds, organomercury compounds and organolithium compounds [12,13,18]. 

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