Electrophilic compounds allylstannane

Allylalwn. This compound is a useful Lewis acid for activation of electrophiles containing oxygen to allylation with allylstannanes. It is usually more effective than BF3 etherate. ... 

Allylstannanes rapidly undergo the Kocheshkov comproportionation reaction with SnCU, even at -50 °C. The initial product is apparently formed with allylic inversion, but further transmetallation may give other allylic isomers.35 The SnCl3 group which is formed enhances the electrophilic power of the allyl group. This has been exploited in aromatic allylation (equation 9-13),36 and transmetallations of this type provide the basis for some, but not all, of the examples of the catalysis of the allylation of carbonyl compounds by allylstannanes in the presence of Lewis acids37,38 (Section 9.1.3.4). 

In the presence of a Lewis acid, allylstannanes couple with various electrophiles such as aldehydes (see Section 9.1.3.4), acetals, a,p-unsaturated ketones and nitro compounds (e.g. equation 9-19), and bis(diethylaluminium) sulfate is reported to be a better catalyst than boron trifluoride.48... 

Allylstannanes react with benzenediazonium tetrafluoroborate to give the allylazo compounds (whereas the allylsilanes react only with the more strongly electrophilic mono- or di-nitrobenzenediazonium salts).53... 

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