Organolead compounds, preparation

Organolead compounds with a carboxylic acid function bound to the alkyl group can be prepared by addition of Ph3PbOH to ketenes162 ... 

Cycloaddition reactions are used to prepare organolead compounds with functionalized substituents. (Triphenylplumbyl)pyrazole, 95, can be prepared from triorganoplumbylalkynes by 1,3-dipolar cycloadditions with diazomethane196 ... 

Functional organolead compounds containing a C—Cl bond can also be prepared by special methods165 ... 

Functional organolead compounds containing C—F bonds can be prepared when R3PbCl reacts with CgFsBr in the presence of P(NEt3)3 to give RsPbCgFs. 

The only non-antiknock use of organolead compounds has been in the preparation of RHgX for application as seed disinfectants and for the control of fungi114. Thiomethyl... 

Furthermore, arylthiophenes have been prepared using the Stille coupling of hypervalent iodonium salts [96] or organolead compounds [97, 98] as electrophiles in place of aryl or vinyl halides and triflates. Hypervalent iodonium salts are sufficiently reactive to undergo coupling at room temperature. 

In the last few years, the interest in organolead(rv) compounds has moved from preparative aspects more to the analytical detection of such compounds or their decomposition products. On the other hand, the synthesis and characterization of low-valent organolead compounds has experienced an impressive increase numerous remarkable results have been achieved, and these constitute the major part of this survey. 

A. L. Prokhorova, in Preparation and Uses of Organolead Compounds, NIITEKhIM, Moscow, 1972, pp. 3-23 (Russian). 

As was mentioned in Section 1, the first synthesis of an organolead compound was reported by Lowig 210>211), who synthesized tetraethyllead by the reaction of a sodium-lead alloy with ethyl iodide. Some 35 years later, Polis 247,248) prepared the first aryl lead derivative by the reaction of bromobenzene with a sodium-lead alloy. Since 1923, the sodium-lead alloy-ethyl chloride reaction has been used for the commercial production of tetraethyllead. A similar reaction has also been used for the commercial production of tetramethyllead since 1960. The sodium-lead alloy-alkyl chloride reaction is discussed in Section 6. 

Organolead derivatives prepared in recent years by one or more of the above reactions are the azides 208>, cyanides 123>, fulminates 45>, arsinates 171), sulfides 104>, alkoxides 242>, peroxides 263>, amines 231>, and phosphines, arsines, and stibines 280-281) The alkoxide 105>, hydride 231> and amine 231> derivatives of organolead undergo reaction with various unsaturated organic compounds to form novel organolead compounds, many of which are not synthesizable by other methods. 

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