Chemistry and Application of Phosphonium and Arsonium Ylide(ⅩⅧ)--Stereoselective Syntheses of (Z)-3-Perfluoroalkyl--4-(3-Carboethoxy-2-f uranyl)-3-Butenoates

高等学校化学研究 ›› 1992, Vol. 8 ›› Issue (3): 224-230.

Chemistry and Application of Phosphonium and Arsonium Ylide(ⅩⅧ)--Stereoselective Syntheses of (Z)-3-Perfluoroalkyl--4-(3-Carboethoxy-2-f uranyl)-3-Butenoates

DING Wei-yu, CAO Wei-guo, ZHU Dian-kui, TONG Wei-qi

Department of Chemistry, Shanghai University of Science and Technology, Shanghai, 201800

收稿日期:1991-06-24 出版日期:1992-08-24 发布日期:2011-09-09
基金资助:
Supported by the National Natural Science Foundation of China;For part XVII of theseries,see Chinese J.of Chem.(tobepublished)

Chemistry and Application of Phosphonium and Arsonium Ylide(ⅩⅧ)--Stereoselective Syntheses of (Z)-3-Perfluoroalkyl--4-(3-Carboethoxy-2-f uranyl)-3-Butenoates

DING Wei-yu, CAO Wei-guo, ZHU Dian-kui, TONG Wei-qi

Department of Chemistry, Shanghai University of Science and Technology, Shanghai, 201800

Received:1991-06-24 Online:1992-08-24 Published:2011-09-09
Supported by:
Supported by the National Natural Science Foundation of China;For part XVII of theseries,see Chinese J.of Chem.(tobepublished)

摘要/Abstract

摘要： The stereoselective syntheses of (Z)-methyl 3-perfluoroalkyl-4-(3-carboethoxy-2-furanyl)-3-butenoates 5a-c were investigated. The reaction of (3-carboethoxy-2-fu-ranyl)-methyltriphenylphosphonium bromide 1 with methyl 2-perfluoroalkynoates 2a-c in the presence of K₂CO₃at room temperature gives two adducts, (E)-methyl 3-per-fluoroalkyl-4-(3-carboethoxy-2-furanyl)-2-triphenylphosphoranylidene-3-butenoates 3a-c and (E)-methyl 3-perfluoroalkyl-4-(3-carboethoxy-2-furanyl)-4-triphenylphos-phoranylidene-2-butenoates 4a-c. (Z)-Methyl 3-perfluoroalkyl-4-(3-carboethoxy-2-furanyl)-3-butenoates 5a-c can be synthesized stereoselectively with high yields when an aqueous DMFsolution of 3c, 4c or a mixture of 3a-b and 4a-b was heated at 140℃ for 8 h.

关键词: (Z)-3-perfluoroalkyl-4-(3-carboethoxy-2-furanyl)-3-butenoate, Phospho-rane, Methyl 2-perfluoroalkynoate, Hydrolysis, Stereoselective synthesis

Abstract: The stereoselective syntheses of (Z)-methyl 3-perfluoroalkyl-4-(3-carboethoxy-2-furanyl)-3-butenoates 5a-c were investigated. The reaction of (3-carboethoxy-2-fu-ranyl)-methyltriphenylphosphonium bromide 1 with methyl 2-perfluoroalkynoates 2a-c in the presence of K₂CO₃at room temperature gives two adducts, (E)-methyl 3-per-fluoroalkyl-4-(3-carboethoxy-2-furanyl)-2-triphenylphosphoranylidene-3-butenoates 3a-c and (E)-methyl 3-perfluoroalkyl-4-(3-carboethoxy-2-furanyl)-4-triphenylphos-phoranylidene-2-butenoates 4a-c. (Z)-Methyl 3-perfluoroalkyl-4-(3-carboethoxy-2-furanyl)-3-butenoates 5a-c can be synthesized stereoselectively with high yields when an aqueous DMFsolution of 3c, 4c or a mixture of 3a-b and 4a-b was heated at 140℃ for 8 h.

Key words: (Z)-3-perfluoroalkyl-4-(3-carboethoxy-2-furanyl)-3-butenoate, Phospho-rane, Methyl 2-perfluoroalkynoate, Hydrolysis, Stereoselective synthesis

DING Wei-yu, CAO Wei-guo, ZHU Dian-kui, TONG Wei-qi . Chemistry and Application of Phosphonium and Arsonium Ylide(ⅩⅧ)--Stereoselective Syntheses of (Z)-3-Perfluoroalkyl--4-(3-Carboethoxy-2-f uranyl)-3-Butenoates[J]. 高等学校化学研究, 1992, 8(3): 224-230.

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Chemistry and Application of Phosphonium and Arsonium Ylide(ⅩⅧ)--Stereoselective Syntheses of (Z)-3-Perfluoroalkyl--4-(3-Carboethoxy-2-f uranyl)-3-Butenoates

Chemistry and Application of Phosphonium and Arsonium Ylide(ⅩⅧ)--Stereoselective Syntheses of (Z)-3-Perfluoroalkyl--4-(3-Carboethoxy-2-f uranyl)-3-Butenoates

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