| 第五、六族元素的有机化合物在有机合成中应用的研究 XXXIII: 氰基亚甲基三苯基膦、胂与2-全氟炔酸甲酯的反应以及3-全氟烷基-4-氰基-3-丁烯酸甲酯的立体选择性合成 |
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| 引用本文： | 丁维钰,浦家齐,张平生.第五、六族元素的有机化合物在有机合成中应用的研究 XXXIII: 氰基亚甲基三苯基膦、胂与2-全氟炔酸甲酯的反应以及3-全氟烷基-4-氰基-3-丁烯酸甲酯的立体选择性合成[J].化学学报,1987,45(1):47-51. |
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| 作者姓名： | 丁维钰 浦家齐 张平生 |
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| 作者单位： | 上海科学技术大学化学系 |
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| 摘 要： | 氰基亚甲基三苯基胂(1)与2-全氟炔酸甲酯(2)反应,生成加合产物2-三苯胂基-3-全氟烷基-4-氰基丁烯-3-酸甲酯(3)通过3的水解,立体选择性地合成了3-全氟烷基-4-氰基-3-丁烯酸甲酸甲酯5(Z),6(E)],Z:E约为95:5.氰基亚甲基三苯基膦(7)与2亦可反应,生成加合产物2-三苯基膦叉-3-全氟烷基-4-氰基丁烯-3-酸甲酯的顺式和反式异构体(8)和(9).总产率在90%左右.8与9的比例受反应介质极性的影响,若溶剂极性增大,则有利于8的生成.
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| 关 键 词： | 甲叉 羧酸酯 羧酸酯 有机化合物 氰基 氰基 三苯基膦 三苯基 有机合成 立体选择性 |
Studies on the application of elemento-organic compounds of the fifth and sixth groups in organic syntheses XXXIII: Reactions of cyanomethylenetriphenylphosphorane and arsorane with methyl perfluoro-2-alkynoates and stereoselective synthesis of methyl 3-p |
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| DING WEIYU,PU JIAQI,ZHANG PINGSHENG.Studies on the application of elemento-organic compounds of the fifth and sixth groups in organic syntheses XXXIII: Reactions of cyanomethylenetriphenylphosphorane and arsorane with methyl perfluoro-2-alkynoates and stereoselective synthesis of methyl 3-p[J].Acta Chimica Sinica,1987,45(1):47-51. |
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| Authors: | DING WEIYU PU JIAQI ZHANG PINGSHENG |
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| Abstract: | Addition of Ph3As+ CH-CN with RCYCCO2Me (R = CF3, C2F5, n-C3F7) followed by hydrolysis of the adducts gave NCCH:CRCH2CO2Me (Z/E = 95/5). Similar reaction of Ph3P:CHCN with RCYCCO2Me gave adducts Ph3P:C(CO2Me)CR:CHCN and their Z/E ratio was influenced by the polarity of the solvents. |
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| Keywords: | METHYLENE CARBOXYLIC ACID ESTER CARBOXYLIC ACID ESTER ORGANIC COMPOUNDS CYANO GROUP CYANO GROUP TRIPHENYLPHOSPHINE TRIPHENYL GROUP ORGANIC SYNTHESIS STEREOSELECTIVITY |
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