Silver Homoenolate

A silocyclopropane reacts with an allylitr chloride in the presence of AgF in aqueous ethanol to give an allylated product Eq. (55) [55]. In this case, the structure of the product does not reflect the regiochemistry of the nucleophilic attack on the starting allyl halide. 

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Palladium Homoenolates Generated In Situ 1.14.7J Silver Homoenolates... 

Siloxycyclopropanes are known as homoenolate anion equivalents and have been favorably utilized in organic synthesis. Murai, Sonoda, and coworkers found that desi-lylative dimerization of the siloxycyclopropanes occurs on exposure to AgBp4 [26a], The reaction of 54 gives 1,6-diketone 55 in good yield (Sch. 13). The 8-silver ketone 56 is considered to be a key intermediate in the dimerization. The intermediary ver ketone, generated from siloxycyclopropane 57 and AgP, can be successfully trapped with allyl chloride to afford a (5,e-unsaturated ketone 58 [26b]. 

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