Plumbyl compounds, metallated

Alkaline and alkaline earth metal-14 compounds TABLE 4. Representative metaUated plumbyl compounds... 

The use of heavy metal reagents in the olefination of carbonyl compounds is in its infancy. However. Kauffmann and co-workers have shown that the phenyl-thio(triphenyl-stannyl or -plumbyl)methyl-lithiums (170) react with benz-aldehyde to give mixtures of threo- (171) and erythro- adducts (173). After the isomers are separated, each is capable of being converted into the ( )- or (Z)-p-phenylthiostyrene, (172) or (174), respectively, stereospecifically, as shown in Scheme 23. 

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