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Ph3P/CF3CCl3作为一个新的羰基烯烃化试剂的研究——一锅法合成烯烃RCH=CClCF3
One Pot Synthesis of Trifluoromethyl Substituted Olefins by Using Ph3p/CF3CCl3 as a New Carbonyl Olefination Reagents
【摘要】 Ph3P/CF3CCl3与醛在室温下一锅反应生成三氟甲基取代的烯烃RCH=CClCF3(3)。芳香醛及α,β-不饱和醛的反应显示高度立体选择性,给出Z式异构体。而饱和脂肪醛的反应立体选择性较低,Z与E式异构体的比例为2:1至3:1。反应可能是经由叶立德Ph3P-CClCF3的Wittig型反应。本工作表明,Pa3P/CF3CCl3可以作为在十分温和的条件下向有机分子中引入=CClCF3结构单元的方便试剂。
【Abstract】 An one pot synthesis of trifluoromethyl substituted olefins by reaction of Ph3P/CF3CCl3 with aldehydes at room temperature was reported. The reactions with aromatioand α,β-unsaturated aliphatic aldehydes are highly stereoselective and give Z isomersof the olefins while the reactions with aliphatic aldehydes give Z and E isomers in 2:1to 3:1 ratios. The reaction might proceed via a phosphorus ylide Ph3 P--CCICF3 which wasgenerated in situ and then underwenta Wittig type of reaction with aldehydes. ThusPh3P/CF3CCl3 may serve as a convenient reagent for transferring a CF3CCl unit into anorganic molecule under very mild conditions.
- 【文献出处】 化学学报 ,Acta Chimica Sinica , 编辑部邮箱 ,1989年04期
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