ACETYLENIC ACIDS .4. REACTIONS OF ALKOXY-SUBSTITUTED PHENYLPROPIOLIC ACIDS AND ESTERS WITH SULFUR HALIDES, PARTICULARLY THIONYL CHLORIDE

被引:16
作者
BONNIN, CM
CADBY, PA
FREEMAN, CG
WARD, AD
机构
[1] Department of Organic Chemistry, University of Adelaide, Adelaide, SA, 5001
关键词
D O I
10.1071/CH9790833
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
3, 4-Dialkoxy-substituted phenylpropiolic acids and esters react with thionyl chloride to give good yields of substituted 1-benzothiophen systems. Similar reactions of m- and p-methoxyphenylpropiolic acids and 3, 4, 5-trimethoxyphenylpropiolic acid, which yield mixtures of products, are reported. In contrast, 2, 5- and 2, 3-dimethoxyphenylpropiolic acids gave mixtures in which a coumarin is the major product. The effect of adding pyridine to the reaction mixture is outlined. Reactions involving sulfur monochloride and sulfur dichloride generally gave much lower yields of these products. Attempts to form organometallic intermediates from the 3-chloro-1-benzothiophen products were unsuccessful. © 1979, CSIRO. All rights reserved.
引用
收藏
页码:833 / 847
页数:15
相关论文
共 50 条
[21]   PHOSPHONIC ACIDS .4. PREPARATION AND REACTIONS OF BETA-KETOPHOSPHONATE AND ENOL PHOSPHATE ESTERS [J].
JACOBSON, HI ;
GRIFFIN, MJ ;
PREIS, S ;
JENSEN, EV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (10) :2608-2612
[22]   DERIVATIVES OF AROMATIC SULFINIC ACIDS .4. ABSOLUTE CONFIGURATIONS OF ASYMMETRIC SULFUR IN EPIMERIC SULFINIC ESTERS [J].
HERBRANDSON, H ;
CUSANO, CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (09) :2124-&
[23]   MASS SPECTROMETRIC STUDIES .4. ESTERS OF MONOMETHYL-SUBSTITUTED LONG CHAIN CARBOXYLIC ACIDS [J].
RYHAGE, R ;
STENHAGEN, E .
ARKIV FOR KEMI, 1960, 15 (04) :291-315
[24]   Copper-Catalyzed Thioetherification Reactions of Alkyl Halides, Triphenyltin Chloride, and Arylboronic Acids with Nitroarenes in the Presence of Sulfur Sources [J].
Rostami, Abed ;
Rostami, Amin ;
Ghaderi, Arash .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17) :8694-8704
[25]   COORDINATION COMPLEXES OF TITANIUM (IV) HALIDES .4. PREPARATION AND INFRARED SPECTRA OF COMPLEXES OF TITANIUM TETRACHLORIDE WITH CHLORINE-SUBSTITUTED ESTERS OF MONOBASIC ACIDS AS LIGANDS [J].
JAIN, SC ;
RIVEST, R .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1962, 40 (12) :2243-&
[26]   HETERODIENE SYNTHESIS .4. SYNTHESIS AND REACTIONS OF SYM-DIHYDROTRIAZINES WITH ESTERS OF ACETYLENEDICARBONIC AND OF PROPIOLIC ACIDS [J].
CHERKASOV, VM ;
KAPRAN, NA ;
ZAVATSKI.VN ;
TSYBA, VT .
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1971, (05) :704-+
[27]   ISOTOPIC EXCHANGE REACTIONS IN LIQUID SULFUR DIOXIDE .4. KINETICS OFTHE CATALYZED S35-EXCHANGE BETWEEN THIONYL CHLORIDE AND SULFUR DIOXIDE [J].
MASTERS, BJ ;
NORRIS, TH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (05) :1346-1352
[28]   REACTIONS OF AZIRINES WITH SULFUR-CONTAINING NUCLEOPHILES .4. INTERACTION OF 2H-AZIRINE WITH MERCAPTO-SUBSTITUTED ACIDS - REACTION OF AZIRIDINYLALKYLSULFIDES WITH CARBOXYLIC-ACIDS AND THEIR CHLORIDES [J].
ELKINSON, RS ;
EREMEEV, AV .
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1986, (02) :206-211
[29]   THE SYNTHESIS OF OMEGA-AMINOALKYL-SUBSTITUTED SILANES .4. SOME REACTIONS OF SILANES WITH PHENOLS AND ACIDS [J].
SARATOV, IE ;
SHPAK, IV ;
MARKOV, SA ;
LAZAREV, SY ;
REIKHSFELD, VO .
ZHURNAL OBSHCHEI KHIMII, 1981, 51 (09) :2034-2038
[30]   REACTIONS OF ISOTHIOCYANATES WITH AMINO ACIDS PEPTIDES AND PROTEINS .4. KINETICS OF REACTION OF SUBSTITUTED PHENYLISOTHIOCYANATES WITH GLYCINE [J].
KRISTIAN, P ;
DROBNICA, L .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1966, 31 (03) :1333-&