Reactions of Epoxides with 3,3,4,4-Tetraethoxybut-1-yne Acetylide: Selective Formation of Propargylic and Homopropargylic Alcohols
作者:Leiv Sydnes、Bjarte Holmelid
DOI:10.1055/s-0033-1339326
日期:——
acetylide) followed by hydrolysis gave the expected homopropargylic alcohols in about 80% yield. When the counterion was MgBr+, oxirane-to-aldehyde rearrangement took place before the acetylide reacted and gave propargylic alcohols in good yields in all cases except one; the only exception was ethylene oxide, which gave the homopropargylic alcohol in 70% yield. 3,3,4,4-Tetraethoxybut-1-yne acetylide (TEB–)
摘要 3,3,4,4-四乙氧基丁-1-炔乙炔(TEB –)在多种条件下与几种环氧化物反应。当乙炔抗衡离子是锂时,在没有氨和HMPA的情况下什么也没发生,但是TEBLi与环氧乙烷和BF 3的混合物(乙炔中添加了环氧乙烷/ BF 3)反应,然后水解,得到了预期的均丙醇% 让。当抗衡离子为MgBr +时,除一种情况外,在乙炔化物反应之前,环氧乙烷到醛发生了重排,并以良好的收率得到了炔丙醇。唯一的例外是环氧乙烷,它以70%的收率得到均丙炔醇。 3,3,4,4-四乙氧基丁-1-炔乙炔(TEB –)在多种条件下与几种环氧化物反应。当乙炔抗衡离子是锂时,在没有氨和HMPA的情况下什么也没发生,但是TEBLi与环氧乙烷和BF 3的混合物(乙炔中添加了环氧乙烷/ BF 3)反应,然后水解,得到了预期的均丙醇% 让。当抗衡离子为MgBr +时,除一种情况外,在乙炔化物反应之前,环氧乙烷到醛发生了重排,并以良好