Reaction of difluorocarbene with propargyl esters and efficient synthesis of difluorocyclopropyl ketones

被引：26
作者：
Hang, Xiao-Chun [1 ]
Gu, Wei-Peng [1 ]
Chen, Qing-Yun [1 ]
Xiao, Ji-Chang [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2009年 / 65卷 / 32期
关键词：
Difluorocyclopropane; Difluorocyclopropene; Difluorocyclopropyl ketone; Difluorocarbene; RING-OPENING REACTIONS; GEM-DIFLUOROCYCLOPROPANES; FLUORINATED CYCLOPROPANES; CHEMISTRY; DIFLUORO(METHYLENE)CYCLOPROPANES; CYCLOADDITION; DERIVATIVES; TRANSFORMATION; NUCLEOPHILES; ALDEHYDES;
D O I：
10.1016/j.tet.2009.06.019
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Difluorocarbene generated from FSO2CF2CO2SiMe3 (TFDA) at 120 degrees C could reacted with terminal alkynes having an ester group at the a position to the triple bond. Difluorocyclopropenes were further converted to difluorocyclopropyl ketones under alkaline condition. Mechanism for the conversion was studied. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6320 / 6324
页数：5
相关论文
共 45 条
[1]   FROM DIFLUOROCYCLOPROPENE TO DIFLUOROCYCLOPROPYLIDENE [J].
BABIN, D ;
PILORGE, F ;
DELBARRE, LM ;
DEMOUTE, JP .
TETRAHEDRON, 1995, 51 (35) :9603-9610
[2]   GEM-DIFLUOROCYCLOPROPENES BY [1+2] CYCLOADDITION REACTIONS BETWEEN DIFLUOROCARBENE AND ACETYLENES HAVING TERMINAL OR INTERNAL TRIPLE BONDS [J].
BESSARD, Y ;
SCHLOSSER, M .
TETRAHEDRON, 1991, 47 (35) :7323-7328
[3]   Heterocycles from alkylidenecyclopropanes [J].
Brandi, A ;
Cicchi, S ;
Cordero, FM ;
Goti, A .
CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269
[4]   Chemistry of difluorocarbene: Synthesis and conversion of difluoro(methylene)cyclopropanes [J].
Cheng, Zhan-Ling ;
Xiao, Ji-Chang ;
Liu, Chao ;
Chen, Qing-Yun .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (24) :5581-5587
[5]   Difluorocarbene chemistry:: A simple transformation of 3,3-gem-difluorocyclopropenes to cyclopropenones [J].
Cheng Zhan-Ling ;
Chen Qing-Yun .
CHINESE JOURNAL OF CHEMISTRY, 2006, 24 (09) :1219-1224
[6]   Difluorocarbene chemistry:: Synthesis of gem-difluorocyclopropenyl ketones and gem-difluorinated dihydrofurans [J].
Cheng, ZL ;
Chen, QY .
SYNLETT, 2006, (03) :478-480
[7]  
Cheng ZL, 2005, J FLUORINE CHEM, V126, P39, DOI 10.1016/j.jfluchem.2004.10.003
[8]   Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA): a new, highly efficient difluorocarbene reagent [J].
Dolbier, WR ;
Tian, F ;
Duan, JX ;
Lia, AR ;
Ait-Mohand, S ;
Bautista, O ;
Buathong, S ;
Baker, JM ;
Crawford, J ;
Anselme, P ;
Cai, XH ;
Modzelewska, A ;
Koroniak, H ;
Battiste, MA ;
Chen, QY .
JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (03) :459-469
[9]   Structure, synthesis, and chemical reactions of fluorinated cyclopropanes and cyclopropenes [J].
Dolbier, WR ;
Battiste, MA .
CHEMICAL REVIEWS, 2003, 103 (04) :1071-1098
[10]   Synthesis of cyclopropane containing natural products [J].
Donaldson, WA .
TETRAHEDRON, 2001, 57 (41) :8589-8627
12345