ORGANIC-REACTIONS CATALYZED BY SOLID SUPERACIDS .5. PERFLUORINATED SULFONIC-ACID RESIN (NAFION-H) CATALYZED INTRAMOLECULAR FRIEDEL-CRAFTS ACYLATION

被引:62
作者
YAMATO, T
HIDESHIMA, C
PRAKASH, GKS
OLAH, GA
机构
[1] UNIV SO CALIF, DONALD P & KATHERINE B LOKER HYDROCARBON RES INST, LOS ANGELES, CA 90089 USA
[2] UNIV SO CALIF, DEPT CHEM, LOS ANGELES, CA 90089 USA
关键词
D O I
10.1021/jo00012a033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nafion-H, a perfluorinated sulfonic acid resin, catalyzed the intramolecular Friedel-Crafts acylation of diarylalkane-2-carboxylic acids and arylalkanoic acids in refluxing p-xylene to provide cyclic ketones. The reactions were clean, and the water that was formed as a byproduct did not deactivate the catalyst. It was also found that the intramolecular acylation of the corresponding acid chlorides occurred under much milder reaction conditions. The mechanism of the reaction is discussed.
引用
收藏
页码:3955 / 3957
页数:3
相关论文
共 15 条
[1]  
COPE AC, 1948, J AM CHEM SOC, V70, P32
[2]   ZUR ELEKTROPHILEN AROMATENSUBSTITUTION .25. CARBOXYLIC TRIFLUOROMETHANESULFONIC ANHYDRIDES AS HIGHLY EFFECTIVE ACYLATION AGENTS - PERFLUOROALKANESULFONIC ACID-CATALYZED ACYLATION OF ARENES [J].
EFFENBERGER, F ;
SOHN, E ;
EPPLE, G .
CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (03) :1195-1208
[3]  
EFFENBERGER F, 1972, ANGEW CHEM INT EDIT, V19, P7
[4]  
Effenberger F., 1972, ANGEW CHEM INT EDIT, V11, P299
[5]   SYNTHESIS OF POLYALKYL-1-TETRALONES AND CORRESPONDING NAPHTHALENES [J].
EISENBRAUN, EJ ;
HINMAN, CW ;
SPRINGER, JM ;
BURNHAM, JW ;
CHOU, TS ;
FLANAGAN, PW ;
HAMMING, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (17) :2480-+
[6]   ACTIVATED METABOLITES OF CARCINOGENIC HYDROCARBONS [J].
HARVEY, RG .
ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (07) :218-226
[7]   A CONVENIENT, MILD METHOD FOR THE CYCLIZATION OF 3-ARYLAKANOIC AND 4-ARYLALKANOIC ACIDS VIA THEIR TRIFLUOROMETHANESULFONIC ANHYDRIDE DERIVATIVES [J].
HULIN, B ;
KOREEDA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (01) :207-209
[8]  
Johnson W.S., 1944, ORG REACTIONS, V2, P114
[9]   STUDIES IN POLYPHOSPHORIC ACID CYCLIZATIONS [J].
KOO, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (08) :1891-1895
[10]  
METZ G, 1972, SYNTH-INT J METHODS, P612