Reactions ofgem-Dibromo Compounds with Trialkylmagnesate Reagents to Yield Alkylated Organomagnesium Compounds
作者:Atsushi Inoue、Junichi Kondo、Hiroshi Shinokubo、Koichiro Oshima
DOI:10.1002/1521-3765(20020402)8:7<1730::aid-chem1730>3.0.co;2-6
日期:2002.4.2
The reaction of gem-dibromocyclopropanes 5 with nBu(3)MgLi affords butylated cyclopropylmagnesium species that can be trapped with various electrophiles. The reaction of dibromomethylsilanes 12 requires the addition of a catalytic amount of CuCN.2LiCl for smooth migration of the alkyl groups. The resultant alpha-silylpentylmagnesium compounds 16 react with electrophiles, such as acyl chlorides or alpha.beta-unsaturated ketones to afford alpha- or gamma-silyl ketones, respectively. Treatment of dibromodisilylmethanes with Me3MgLi yields 1-bromo-1,1-disilylethanes 25 that can be converted into 1,1-disilylethenes 29 by dehydrobromination.