Synthesis of propargylic ethers via Lewis-acid mediated nucleophilic substitution of propargylic esters

被引:21
作者
Bartels, A [1 ]
Mahrwald, R [1 ]
Quint, S [1 ]
机构
[1] Humboldt Univ, Inst Organ & Bioorgan Chem, D-10155 Berlin, Germany
关键词
alkynes; substitution; ethers; catalysis;
D O I
10.1016/S0040-4039(99)01250-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct displacement of propargylic esters is reported. 10 mol% of TiCl4 were used to carry out this novel, nucleophilic substitution. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5989 / 5990
页数:2
相关论文
共 18 条
[1]  
ALTENBACH HJ, 1991, COMPREHENSIVE ORGANI, V6, P829
[2]   SYNTHESIS OF SOME NOVEL TRIFLUOROMETHANESULFONATES AND THEIR REACTIONS WITH ALCOHOLS [J].
BEARD, CD ;
BAUM, K ;
GRAKAUSK.V .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (21) :3673-3677
[4]   PALLADIUM CATALYZED CROSS-COUPLING AND TANDEM CYCLIZATION-COUPLING OF ALPHA-HALO(THIO)ETHERS WITH ORGANOTINS [J].
BHATT, RK ;
SHIN, DS ;
FALCK, JR ;
MIOSKOWSKI, C .
TETRAHEDRON LETTERS, 1992, 33 (34) :4885-4888
[5]   DIRECT DISPLACEMENT AND COUPLING OF PROP-2-YNYLIC ACETATES WITH ORGANOCUPRATES [J].
BRINKMEYER, RS ;
MACDONALD, TL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (20) :876-877
[6]  
DENMARK SE, 1991, COMPREHENSIVE ORGANI, V5, P768
[7]   REACTION OF PROPARGYLIC SUBSTRATES WITH ORGANOCOPPER SPECIES - SYNTHETIC ASPECTS [J].
MACDONALD, TL ;
REAGAN, DR ;
BRINKMEYER, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4740-4747
[8]   PALLADIUM(II)-INDUCED CONVERSION OF ALPHA-ACETOXYALKYNES INTO ALPHA,BETA-UNSATURATED ALPHA-ACETOXYKETONES - A NOVEL ACCESS TO ALPHA-DIKETONES [J].
MAHRWALD, R ;
SCHICK, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05) :593-594
[9]  
Malleron J.-L., 1997, HDB PALLADIUM CATALY, DOI DOI 10.1002/anie.201700889
[10]  
MANTIONE R, 1969, B SOC CHIM FR, P4514