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学科主题: 有机氟化学
题名: The synthesis of 2,4-dienyl fluoroalkyl ketones by a tandem three-stage seuence of propargyl 2-fluoroalkylvinyl ether formation, Claisen rearrangement, and allene-to-conjugated diene isomerization
其他题名: 通过串联的2-氟烷基炔丙基烯基醚的制备,Claisen重排, 联烯重排为共扼二烯三步反应合成2,4不饱和含氟烷基酮
作者: Peng WM(彭卫民) ; Zhu SZ(朱仕正)
通讯作者: 朱仕正
刊名: Tetrahedron
发表日期: 2003-01-01
卷: 59, 期:25, 页:4641-4649
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所元素有机化学实验室
英文摘要: A tandem three stages process to a series of trifluoromethyl and halodifluoromethyl 2,4-unsaturated ketones 4a-c is described.This process started with the preparation of 2-fluoroalkyl substituted propargyl vinyl ether 3a-d by treatment of a mixture of individual ethylα-per(poly)fluoroalkyl acetates la-d and propargyl alcohol 2 in CH^2Cl^2 with the mixed base (Na^2CO^3/TEA) at ambient temperature. When heated in toluene at 80℃, these ethers readily underwent a tandem propargyl-allenyl Claisen rearrangement and isomerization of the resultant 3,4-dienone to give 2,4-unsaturated fluoroalkyl ketones 4a-c (Z/E mixture). The reaction of ethyl α-per(poly)fluoroalkyl acetate I with l-phenyl propargyl alcohol 5 in refluxing CH^2Cl^2 in the presence of the mixed base (Na^2CO^3/TEA) directly afforded the cooesponding unsaturated fluoroalkyl ketone 6a-c in one pot. In the presence of NaH, the reaction of ethyl 3-halo-3-fluoroalkylacrylates 8a-b with 1,1-dimethyl propargyl alcohol 9 at -50℃ to 0℃ also gave the unsaturated Huoroalkyl ketones 10a-b in one pot. The difluorovinyl propargyl ether 11 prodnced by reduction of 2-bromodifluoromethyl substituted propargyl vinyl ether 3b rearranged in hot benzene to give the corresponding allene 12 bearing a gem-difluoromethylene group in the middle of the aliphatic chain.
语种: 英语
相关网址: 查看原文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/14300
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

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Recommended Citation:
Peng WM,Zhu SZ. The synthesis of 2,4-dienyl fluoroalkyl ketones by a tandem three-stage seuence of propargyl 2-fluoroalkylvinyl ether formation, Claisen rearrangement, and allene-to-conjugated diene isomerization[J]. Tetrahedron,2003,59(25):4641-4649.
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