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

✍ Scribed by Yan-Chang Shen; Guo-Fang Jiang

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 262 KB
Volume: 20
Category: Article
ISSN: 0256-7660
DOI: 10.1002/cjoc.20020201137

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✦ Synopsis

Abstract

Diethyl (1‐cyanoethyl) phosphorate 1 was reacted with n‐butyl‐lithium in tetrahydrofuran (THF) at ‐ 78 °C and the resulting carbanion 2 reacted with perfluoroalkanoic add anhydride to afford perfluoroacylated phosphorate 3. Without isolation 3 was attacked by Grignard reagents giving perfluoroalkylated α, β‐unsaturated nitriles in 46%‐88% yields with high Z‐stereoselectivity (Z: E = 89–62:11–38).

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✍ K. FUNABIKI; Y. FUKUSHIMA; T. INAGAKI; E. MURATA; M. MATSUI; K. SHIBATA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 39 KB 👁 1 views