ALCL3-N,N-DIMETHYLANILINE - A NOVEL BENZYL AND ALLYL ETHER CLEAVAGE REAGENT

被引:34
作者
AKIYAMA, T
HIROFUJI, H
OZAKI, S
机构
关键词
D O I
10.1246/bcsj.65.1932
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A combination system of AlCl3-N,N-dimethylaniline was found to cleave benzyl ethers readily to give parent alcohols in excellent yields. The system also cleaved allyl as well as methyl ethers. Numerous functional groups such as benzoyloxy, phenylthio, and olefinic double bond were not affected. Comparisons of AlCl3-N,N-dimethylaniline and AlCl3-anisole were described.
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页码:1932 / 1938
页数:7
相关论文
共 34 条
[11]   HARD ACID AND SOFT NUCLEOPHILE SYSTEM - NEW EFFICIENT METHOD FOR REMOVAL OF BENZYL PROTECTING GROUP [J].
FUJI, K ;
ICHIKAWA, K ;
NODE, M ;
FUJITA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1661-1664
[12]  
FUJI K, 1980, CHEM PHARM BULL, V28, P3662
[13]   STEROIDAL LARIAT ETHERS - A NEW CLASS OF MACROCYCLES AND THE CRYSTAL-STRUCTURE OF N-(CHOLESTERYLOXYCARBONYL)AZA-15-CROWN-5 [J].
GOKEL, GW ;
HERNANDEZ, JC ;
VISCARIELLO, AM ;
ARNOLD, KA ;
CAMPANA, CF ;
ECHEGOYEN, L ;
FRONCZEK, FR ;
GANDOUR, RD ;
MORGAN, CR ;
TRAFTON, JE ;
MILLER, SR ;
MINGANTI, C ;
EIBAND, D ;
SCHULTZ, RA ;
TAMMINEN, M .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (14) :2963-2968
[14]  
GREENE TW, 1981, PROTECTIVE GROUPS OR, pCH1
[15]   REDUCTION OF ACETALS WITH TICL4-LIALH4 [J].
ISHIKAWA, H ;
MUKAIYAMA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (07) :2059-2063
[16]  
KARIYONE K, 1970, TETRAHEDRON LETT, P2885
[17]  
KIKUGAWA Y, 1979, CHEM PHARM BULL, V27, P2405
[18]   SYNTHETIC APPROACH TO CYTOCHALASINS [J].
KIM, MY ;
STARRETT, JE ;
WEINREB, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (26) :5383-5389
[19]   EFFICIENT REMOVAL OF N-BENZYLOXYCARBONYL GROUP BY A PUSH-PULL MECHANISM USING THIOANISOLE-TRIFLUOROACETIC ACID, EXEMPLIFIED BY A SYNTHESIS OF MET-ENKEPHALIN [J].
KISO, Y ;
UKAWA, K ;
AKITA, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (03) :101-102
[20]  
KISO Y, 1980, CHEM PHARM BULL, V28, P673