148259-35-2Relevant academic research and scientific papers
Reactions of gem-dibromo compounds with trialkylmagnesate reagents to yield alkylated organomagnesium compounds
Inoue, Atsushi,Kondo, Junichi,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 1730 - 1740 (2007/10/03)
The reaction of gem-dibromocyclopropanes 5 with nBu3MgLi 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 Me3MgLi yields 1-bromo- 1,1-disilylethanes 25 that can be converted into 1,1-disilylethenes 29 by dehydrobromination.
tert-Butyldimethylsilyldihalomethyllithium as a dihalomethylene dianion synthon. 1,3-Rearrangement and 1,4-rearrangement of silyl group from carbon to oxide
Shinokubo, Hiroshi,Miura, Katsukiyo,Oshima, Koichiro,Utimoto, Kiitiro
, p. 503 - 514 (2007/10/03)
One-pot synthesis of R1CH(OSiMe2-t-Bu)CX2CH(OH)R2 (X = Cl, Br) by successive addition of two different aldehydes (R1CHO and R2CHO) has been achieved starting from tert-butyldimethylsilyldihalomethyllithium. Treatment of a THF solution of the title carbanion (X = Cl) with p-MeOC6H4CHO or n-BuCHO followed by an addition of HMPA and benzaldehyde gave the corresponding 1,3-diol monosilyl ether in 83% or 45% yield, respectively. The use of oxirane in place of aldehyde as the first electrophile followed by addition of benzaldehyde provided 1,4-diol monosilyl ether.
tert-Butyldimethylsilyldichloromethyllithium as a dichloromethylene dianion synthon. 1,3-Rearrangement of silyl group from carbon to oxide
Shinokubo, Hiroshi,Miura, Katsukiyo,Oshima, Koichiro,Utimoto, Kiitiro
, p. 1951 - 1954 (2007/10/02)
One-pot synthesis of R1CH(OSiMe2-t-Bu)CCl2CH(OH)R2 by successive addition of two different electrophiles has been achieved starting.
