| Reaction of Grignard Reagents with Diethyl Perfluoroacyl (1-Cyanoethyl)phosphonates. Synthesis of Perfluoroalkylated α,β-Unsaturated Nitriles with Predominant Z-Selectivity |
| |
| 引用本文： | 沈延昌,江国防. Reaction of Grignard Reagents with Diethyl Perfluoroacyl (1-Cyanoethyl)phosphonates. Synthesis of Perfluoroalkylated α,β-Unsaturated Nitriles with Predominant Z-Selectivity[J]. 中国化学, 2002, 20(11): 1375-1378. DOI: 10.1002/cjoc.20020201137 |
| |
| 作者姓名： | 沈延昌 江国防 |
| |
| 作者单位： | SHEN，Yan-Chang JIANG，Guo-FangState Key Laboratory of Organometallic Chemistry，Shanghai Institute of Organic Chemistry，Chinese Academy of Sciences，Shanghai 200032，China |
| |
| 基金项目： | theNationalNaturalScienceFoundationofChina (No.2 9972 0 46 )andChineseAcademyofSciences |
| |
| 摘 要： | ＩｎｔｒｏｄｕｃｔｉｏｎＲｅｃｅｎｔｌｙｍｕｃｈａｔｔｅｎｔｉｏｎｈａｓｂｅｅｎｄｅｖｏｔｅｄｔｏｔｈｅｓｙｎｔｈｅｓｉｓｏｆα ,β ｕｎｓａｔｕｒａｔｅｄｎｉｔｒｉｌｅｓｓｉｎｃｅｔｈｅｙａｒｅｉｍ ｐｏｒｔａｎｔｓｔｒｕｃｔｕｒａｌｆｅａｔｕｒｅｏｆｓｅｖｅｒａｌｎａｔｕｒａｌｌｙｏｃｃｕｒｒｉｎｇｂｉ ｏｌｏｇｉｃａｌｌｙａｃｔｉｖｅｃｏｍｐｏｕｎｄｓ .1,2 Ｔｈｅｉｎｔｒｏｄｕｃｔｉｏｎｏｆｆｌｕｏ ｒｉｎｅｏｒｔｒｉｆｌｕｏｒｏｍｅｔｈｙｌｇｒｏｕｐｉｎｔｏｂｉｏｌｏｇｉｃａｌｌｙａｃｔｉｖ…
|
| 关 键 词： | perfluoroalkylated α β-unsaturated nitrile Grignard reagent diethyl (1-cyanoethyl)phosphonate Z-selectivity |
Reaction of Grignard Reagents with Diethyl Perfluoroacyl (1‐Cyanoethyl) phosphonates. Synthesis of Perfluoroalkylated α, β‐Unsaturated Nitriles with Predominant Z‐Selectivity |
| |
| SHEN,Yan-Chang JIANG,Guo-FangState Key Laboratory of Organometallic Chemistry. Reaction of Grignard Reagents with Diethyl Perfluoroacyl (1‐Cyanoethyl) phosphonates. Synthesis of Perfluoroalkylated α, β‐Unsaturated Nitriles with Predominant Z‐Selectivity[J]. Chinese Journal of Chemistry, 2002, 20(11): 1375-1378. DOI: 10.1002/cjoc.20020201137 |
| |
| Authors: | SHEN Yan-Chang JIANG Guo-FangState Key Laboratory of Organometallic Chemistry |
| |
| Affiliation: | SHEN,Yan-Chang JIANG,Guo-FangState Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China |
| |
| 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). |
| |
| Keywords: | perfluoroalkylated α β‐unsaturated nitrile Grignard reagent diethyl (l‐cyanoethyl)phosphonate Z‐selectivity |
| 本文献已被 CNKI 等数据库收录！ |
