Reaction of 1,4-bis(trimethylsilyl)-2-butene with aromatic aldehydes catalyzed by TiCl4: an approach to (1-vinylallyl)benzene type derivatives
作者:Qianqian Ding、Anne-Sophie Chapelon、Cyril Ollivier、Maurice Santelli
DOI:10.1016/j.tetlet.2006.03.179
日期:2006.6
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
1,4-双(三甲基甲硅烷基)-2-丁烯1在四氯化钛存在下可与烷基醛和芳族醛反应生成α-(三甲基甲硅烷基)甲基均烯丙基醇和(1-乙烯基烯丙基)苯型化合物根据存在于芳环上的每个取代基的相关位置。在最后一种情况下,反应涉及被TiCl 4活化的芳族醛对SE1'进行1,4-双(三甲基甲硅烷基)-2-丁烯的亲电取代,然后进行乙烯基的1,2-迁移。