Direct synthesis of per(poly)fluoroalkylmethyl-substituted electrophilic cyclopropane derivatives

Direct synthesis of per(poly)fluoroalkylmethyl-substituted electrophilic cyclopropane derivatives

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摘要 A convenient and direct per(poly)fluoroalkylmethyl-introducing cyclopropanation reaction was described. In the presence of CrCl3/Fe, per(poly)fluoroalkyl iodides reacted with diethyl allylmalonate and its analogs to give per(poly)fluoroalkylmethyl-substituted electrophilic cyclopropane derivatives in high yields. This reaction was considered to proceed by two steps: radical addition followed by cyclopropanation. A convenient and direct per(poly)fluoroalkylmethyl-introducing cyclopropanation reaction was described. In the presence of CrCl3/Fe, per(poly)fluoroalkyl iodides reacted with diethyl allylmalonate and its analogs to give per(poly)fluoroalkylmethyl-substituted electrophilic cyclopropane derivatives in high yields. This reaction was considered to proceed by two steps: radical addition followed by cyclopropanation.

作者 CHEN, J HU, CM

机构地区 CHINESE ACAD SCI

出处《Chinese Journal of Chemistry》 SCIE CAS CSCD 1995年第4期368-379,共12页 中国化学（英文版）

基金 Project supported by the National Natural Science Foundation of China.

关键词 FLUOROALKYL IODIDE DIETHYL ALLYLMALONATE CRCL3/FE REDOX SYSTEM ADDITION CYCLOPROPANATION FLUOROALKYL IODIDE DIETHYL ALLYLMALONATE CRCL3/FE REDOX SYSTEM ADDITION CYCLOPROPANATION

分类号 O624 [理学—有机化学]

引文网络
相关文献

1Qiao Sheng HU and Chang Ming HU(Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy ofSciences, 354 Fengling Lu, Shanghai, 200032).Addition of Per(poly)fluoroalkyl Iodides to vinyl Cyclopropane Derivatives: Synthesis of Fluoroalkyl Substituted γ,δ-Unsaturated Carbonyl Compounds[J].Chinese Chemical Letters,1997,8(7):565-568.
2Xu Hong CHENG,Zheng Ning LI,Hui Lin CHEN(Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023).THE　APPLICATION　OF　Cu（facam）2　TO　THE　ASYMMETRIC　CYCLOPROPANATION　OF　2，5－DIMETHYL－2，4－HEXADIENE[J].Chinese Chemical Letters,1996,7(8):703-705.
3DING Wei-yu ,HAN Zi-heng,CHEN Ya-li,ZOU Yong-jun and LIU Xin(Department of Chemistry, Shanghai University, Shanghai 201800).Stereoselective Synthesis of cis-1, 2-cyclopropane Derivatives[J].Chemical Research in Chinese Universities,1996,12(1):50-55. 被引量：2
4A Novel Synthesis of 2-Per(poly)fluoroalkyl Quinoline[J].厦门大学学报（自然科学版）,1999,38(S1):236-236.
5HU, Qiao-Sheng HU, Chang-MingLaboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.A facile synthesis of per (poly )fluoroalkyl substituted α-amino acid derivatives[J].Chinese Journal of Chemistry,1997,15(3):286-288.
6Zheng, Z,Han, M,Chen, HL.HIGHLY ACTIVE CATALYSTS FOR CYCLOPROPANATION OF TETRAMETHYLETHYLENE[J].Chinese Chemical Letters,1996,7(8):739-740.
7Yu XU,Zhong Yi WANG and Tian Pa YOU(Department of Chemistry, University of Science and Technology of China, Hefei 230026).Catalytic Asymmetric Cyclopropanation using a New Chiral β-Diketone Cu (Ⅱ) Complex as a Catalyst[J].Chinese Chemical Letters,1998,9(7):607-608.
8Er Le ZANG,Ping LI,Bing Fang HU (Department of Applied Chemistry. Beijing Agricultural University, Beijing 100094).STUDIES　ON　THE　CONSTITUENT　OF　THE　ACTIVE　COPPER　CATALYSIA　IN　CYCLOPROPANATION　REACTIONS[J].Chinese Chemical Letters,1994,5(5):423-424.
9Qiao Sheng HU and Chang Ming HU(Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,354 Fengling Lu,Shanghai,200032).Synthesis of Ethyl 3-Fluoroalkyl-3-Halo Acrylate With CH_2N_2[J].Chinese Chemical Letters,1997,8(8):673-676.
10Zheng Ning LI,Zhi Xiu XU,Hui Lin CHEN,Zhuo ZHENG,Yun XU,Xin Quan HU(Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Dalian 116023).Cyclopropanation of 1, 1-Dichloro-4-methyl-1,3-pentadiene with Diazoacetate[J].Chinese Chemical Letters,1997,8(7):559-562.

Chinese Journal of Chemistry

1995年第4期

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Direct synthesis of per(poly)fluoroalkylmethyl-substituted electrophilic cyclopropane derivatives

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