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首页> 外文期刊>Chemistry: A European journal >Highly Efficient Synthesis of Stereodefined Multisubstituted 1,4-Dicyano-and l-Cyano-l,3-butadienes and Their Reactions with Organolithium Reagents
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Highly Efficient Synthesis of Stereodefined Multisubstituted 1,4-Dicyano-and l-Cyano-l,3-butadienes and Their Reactions with Organolithium Reagents

机译：立体定义的多取代1,4-二氰基和1-氰基-1,3-丁二烯的高效合成及其与有机锂试剂的反应

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摘要

Stereodefined multisubstituted 1-cyano-and l,4-dicyano-l,3-buta-diene derivatives were obtained in excellent yields of the isolated product from their corresponding monohalo-and dihalobutadienes and CuCN.This reaction proceeded with high stereoselectivity and retention of the stereochemistry of the starting halobuta-dienes.A study of the utility of the thus-obtained 1-cyano-and 1,4-dicyano-l,3-butadiene derivatives was demonstrated by their reactions with organolithium reagents.2H-Pyrrole or imi-nocyclopentadiene derivatives were formed in high yields from 1-cyano-4-halo-l,3-butadienes and organolithium reagents.When l,4-dicyano-l,3-buta-dienes were treated with organolithium reagents followed by trapping with electrophiles,a tandem process took place to afford 2H-pyrrolyl nitriles in excellent yields.Reduction of 1,4-di-cyano-l,3-butadiene derivatives with LiAlH_4 showed novel reaction patterns relative to normal nitriles.
机译：从其相应的单卤代和二卤代丁二烯和CuCN分离出的产物中，以优异的收率获得了立体定义的多取代的1-氰基和1,4-二氰基-1,3-丁二烯衍生物。通过与有机锂试剂的反应证明了由此获得的1-氰基和1,4-二氰基-1,3-丁二烯衍生物的效用的研究.2H-吡咯或imi-由1-氰基-4-卤代-1,3-丁二烯和有机锂试剂以高收率形成环戊二烯衍生物。将1,4-二氰基-1,3-丁二烯用有机锂试剂处理，然后用亲电试剂捕集，进行了串联反应，以优异的收率获得了2H-吡咯基腈。用LiAlH_4还原1,4-二氰基-1,3-丁二烯衍生物显示出相对于普通腈而言新颖的反应模式。

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