Journal of Organic Chemistry p. 1721 - 1722 (1980)
Update date:2022-08-04
Topics:
Seyferth, Dietmar
Pornet, Jacques
Pentadienyllithium reacts with trimethylchlorosilane to give (2,4-pentadienyl)trimethylsilane, Me3SiCH2CH=CHCH=CH2, as the exclusive product.This silane reacts with aliphatic and aromatic aldehydes and ketones in the presence of TiCl4 in dichloromethane at -40 deg C to give, after hydrolytic workup, exclusively products of the type RR'C(OH)CH2=CHCH=CH2 in good yield.With α,β-unsaturated carbonyl compounds a TiCl4-induced Diels-Alder reaction of the dienylsilane interferes.
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