Reactions
The C–Pb bond is weak and for this reason homolytic cleavage of organolead compounds to free radicals is easy. In its anti-knocking capacity, its purpose is that of a radical initiator. General reaction types of aryl and vinyl organoleads are transmetalation for instance with boronic acids and acid-catalyzed heterocyclic cleavage. Organoleads find use in coupling reactions between arene compounds. They are more reactive than the likewise organotins and can therefore be used to synthesise sterically crowded biaryls.
In oxyplumbation, organolead alkoxides are added to polar alkenes:
- H2C=CH-CN + (Et3PbOMe)n → MeO-CH2-HC(PbEt3)-CN → MeO-CH2-CH2-CN
The alkoxide is regenerated in the subsequent methanolysis and, therefore, acts as a catalyst.
Read more about this topic: Organolead Compound
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