Tetrahedron letters

Reaction of 1, 4-bis (trimethylsilyl)-2-butene with aromatic aldehydes catalyzed by TiCl 4: an approach to (1-vinylallyl) benzene type derivatives

Q Ding, AS Chapelon, C Ollivier, M Santelli

Index: Ding, Qianqian; Chapelon, Anne-Sophie; Ollivier, Cyril; Santelli, Maurice Tetrahedron Letters, 2006 , vol. 47, # 23 p. 3857 - 3860

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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 ...