Qianqian Ding, A. Chapelon, C. Ollivier
Jun 5, 2006
Citations
0
Influential Citations
5
Citations
Journal
Tetrahedron Letters
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.