Reaction of Grignard Reagents with Diethyl Perfluoroacyl( 1-Cyanoethyl ) phosphonates. Synthesis of Perfluoroalkylated α, β-Unsaturated Nitriles with Predominant Z-Selectivity

• 来源期刊: 中国化学(英文版)
• 年，卷（期）: 2002,（11）
• 页码范围: 1375-1378
• 页数: 4页
• 语种: 英文

摘要

Diethyl (1-cyanoethyl)phosphonate 1 was reacted with n-butyllithium in tetrahydrofuran ( THF ) at - 78 ℃ and the resulting carbanion 2 reacted with perfluoroalkanoic acid anhydride to afford perfluoroacylated phosphonate 3. Without isolation 3was attacked by Grognard reagents giving perfluoroalkylated α,β-unsaturated nitries in 46%-88% yields with high Zstereoselectivity(Z:E=89-62:11-38).