120809-73-6Relevant academic research and scientific papers
Synthesis of trisubstituted and tetrasubstituted alkenes via a manganate-induced migration-elimination process
Kakiya, Hirotada,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 10063 - 10069 (2007/10/03)
Preparation of alkenes via a manganate-induced alkylation-elimination sequence was investigated. The reaction of 2-alkoxy-1,1-dibromoalkanes with trialkylmanganates afforded disubstituted or trisubstituted alkenes. Treatment of 2-alkoxy-1,1,1-tribromoalkanes with trialkylmanganates provided trisubstituted or tetrasubstituted alkenes through bromine-metal exchange, transfer of two alkyl groups from manganese to carbon, and successive elimination of metal and the β-alkoxy moieties.
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.
