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Reactions of gem ‐Dibromo Compounds with Trialkylmagnesate Reagents to Yield Alkylated Organomagnesium Compounds
Author(s) -
Inoue Atsushi,
Kondo Junichi,
Shinokubo Hiroshi,
Oshima Koichiro
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020402)8:7<1730::aid-chem1730>3.0.co;2-6
Subject(s) - electrophile , reagent , chemistry , alkylation , silylation , organic chemistry , yield (engineering) , alkyl , catalysis , materials science , metallurgy
The reaction of gem ‐dibromocyclopropanes 5 with n Bu 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⋅2 LiCl for smooth migration of the alkyl groups. The resultant α ‐silylpentylmagnesium compounds 16 react with electrophiles, such as acyl chlorides or α , β ‐unsaturated ketones to afford α ‐ or γ ‐silyl ketones, respectively. Treatment of dibromodisilylmethanes with Me 3 MgLi yields 1‐bromo‐1,1‐disilylethanes 25 that can be converted into 1,1‐disilylethenes 29 by dehydrobromination.