Addition of trimethylsilylmethylmagnesium chloride to α, β-unsaturated carbonyls
1981; Elsevier BV; Volume: 220; Issue: 3 Linguagem: Inglês
10.1016/s0022-328x(00)82282-2
ISSN1872-8561
AutoresRichard T. Taylor, James G. Galloway,
Tópico(s)Organoboron and organosilicon chemistry
ResumoReactions of α,β-unsaturated carbonyl compounds with Me3SiCH2MgCl, prepared from chloromethyltrimethylsilane [1], were examined. Unlike its lithium counterpart (Me3SiCH2Li), which adds to α,β-unsaturatedketones in the 1,2-sense, the Grignard reagent afforts γ silanes via a 1,4-addition sequence. This tendency is accentuated by the addition of Cu2Br2. Addition of the Grignard reagent to α,β-unsaturated aldehydes gives the simple 1,2-addition products.
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