Article ID Journal Published Year Pages File Type
5290078 Tetrahedron Letters 2006 4 Pages PDF
Abstract
1,4-bis(Trimethylsilyl)-2-butene 1 can react with alkyl and aromatic aldehydes in the presence of titanium tetrachloride to give α-(trimethylsilyl)methyl homoallylic alcohols and (1-vinylallyl)benzene type compounds in poor to good yield according to the related position of each substituents present on the aromatic ring. In the last case, the reaction involves a SE2′ type electrophilic substitution of 1,4-bis(trimethylsilyl)-2-butene by aromatic aldehydes activated by TiCl4, followed by a 1,2-migration of a vinyl group.
Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
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