ALIPHATIC HYDROXY-ACIDS .3. SYNTHESES WITH ALKYL 2-ACETOXY-3-CARBOXYPROPIONATES

被引:17
作者
BRETTLE, R
LATHAM, DW
机构
[1] Department of Chemistry, The University, Sheffield
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1968年 / 08期
关键词
D O I
10.1039/j39680000906
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methyl (±)-2-acetoxy-3-carboxypropionate has been prepared from (±)-malic acid and used in crossed Kolbe electrolyses to prepare dimethyl (±)-2-acetoxydodecane-1,12-dioate and three methyl 2-acetoxyalkanoates. Dimethyl and diethyl meso-2,5-diacetoxyadipates have been isolated from the Kolbe electrolyses of methyl and ethyl (±)-2-acetoxy-3-carboxypropionates respectively, and the presence of the corresponding (±)-2,5- diacetoxyadipates has been established. Lithium aluminium hydride reduction of diethyl meso-2,5-diacetoxyadipate gives meso-hexane-1,2,5,6-tetraol.
引用
收藏
页码:906 / &
相关论文
共 23 条
[1]   ANODIC OXIDATION .3. ELECTROLYSIS OF METHYL HYDROGEN CIS-CYCLOPROPANE-1,2-DICARBOXYLATE [J].
BINNS, TD ;
BRETTLE, R ;
COX, GB .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (05) :584-&
[2]   ALIPHATIC HYDROXY-ACIDS .2. SOME TERMINALLY SUBSTITUTED ISO-ACIDS [J].
BRETTLE, R ;
HOLLAND, FS .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (OCT) :3678-&
[3]   Studies in pyrolysis Part I The pyrolysis of derivatives of alpha-acetoxypropionic acid, and related substances [J].
Burns, R ;
Jones, DT ;
Ritchie, PD .
JOURNAL OF THE CHEMICAL SOCIETY, 1935, :400-406
[4]   ASSOCIATION OF SUBSTRATES WITH ALPHA-CHYMOTRYPSIN DIETHYL ALPHA-ACETOXYSUCCINATE AND DIETHYL MALATE [J].
COHEN, SG ;
NEUWIRTH, Z ;
WEINSTEIN, SY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (22) :5306-+
[5]   STUDIES ON SUCCINIC ACIDS .1. PREPARATION OF ALPHA,ALPHA-'-DIALKYL-SUBSTITUTED AND TETRAALKYL-SUBSTITUTED SUCCINIC ACIDS BY KOLBE ELECTROLYSIS [J].
EBERSON, L .
ACTA CHEMICA SCANDINAVICA, 1959, 13 (01) :40-49
[6]  
FEIN ML, 1948, IND ENG CHEM, V40, P537
[7]  
FISHER CH, Patent No. 2374428
[8]   HYDROGENOLYSIS OF CARBOHYDRATES .4. 1,2-O-ISOPROPYLIDENE-D-GLUCOFURANOSE [J].
GORIN, PAJ ;
PERLIN, AS .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1958, 36 (04) :661-666
[9]   THE CONVERSION OF SUCROSE INTO FURAN COMPOUNDS .2. SOME 2-5-DISUBSTITUTED TETRAHYDROFURANS AND THEIR PRODUCTS OF RING SCISSION [J].
HAWORTH, WN ;
JONES, WGM ;
WIGGINS, LF .
JOURNAL OF THE CHEMICAL SOCIETY, 1945, (JAN-) :1-4
[10]  
HORN DHS, 1954, J CHEM SOC, P1461