ADDITION OF TRIMETHYLSILYLMETHYLMAGNESIUM CHLORIDE TO α,β-UNSATURATED CARBONYLS

Article abstract of DOI:10.1016/S0022-328X(00)82282-2

Reactions of α,β-unsaturated carbonyl compounds with Me3SiCH2MgCl, prepared from chloromethyltrimethylsilane <1>, were examined.Unlike its lithium counterpart (Me3SiCH2Li), which adds to α,β-unsaturated ketones in the 1,2-sense, the Grignard reagent afforts γ silanes via a 1,4-addition sequence.This tendency is accenturated by the addition of Cu2Br2.Addition of the Grignard reagent to α,β-unsaturated aldehydes gives the simple 1,2-addition products.