REGIOSPECIFIC ALKYLATION OF TETRONIC ACIDS - FORMATION OF 4-ALKOXY-5H-FURAN-2-ONES AND 2-ALKOXY-5H-FURAN-4-ONES

被引：33

作者：

WENGEL, AS ^{[1
]}

REFFSTRUP, T ^{[1
]}

BOLL, PM ^{[1
]}

机构：

[1] ODENSE UNIV,DEPT CHEM,DK-5230 ODENSE M,DENMARK

来源：

TETRAHEDRON | 1979年 / 35卷 / 18期

关键词：

D O I：

10.1016/0040-4020(79)87037-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Alkoxy-5H-furan-4-ones (7,8) and 4-alkoxy-5H-furan-2-ones (4,5) were prepared regiospecifically and in high yields from tetronic acids (4-hydroxy-5H-furan-2-ones) (2) in the first case by acetylating the 4-OH group and then reacting with trialkyloxonium tetrafluoroborate, and in the second case by alkylating tetrabutylammonium tetronates with dialkyl sulfate, respectively. Direct alkylation of tetronic acids with trialkyloxonium tetrafluoroborate gave in four cases regiospecific 2-O-alkylation, in one case 4-O-alkylation and in two other cases mixtures of 2- and 4-alkoxy derivatives. © 1979.

引用

页码：2181 / 2185

页数：5

共 24 条

[1]

AHMED MG, 1969, CHEM COMMUN, P1389

[2] METHYLATION OF PROTOTROPIC AMBIDENT NUCLEOPHILES - PROTON AS A FORMAL DIRECTING GROUP [J].