A PRACTICAL SYSTEM FOR MANGANESE(III)-MEDIATED ELECTROCHEMICAL SYNTHESIS OF SORBIC ACID PRECURSORS

被引:22
作者
COLEMAN, JP
HALLCHER, RC
MCMACKINS, DE
ROGERS, TE
WAGENKNECHT, JH
机构
[1] Monsanto Company, St. Louis, MO 63167
关键词
D O I
10.1016/S0040-4020(01)87070-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, practical, electrochemical system was developed for the synthesis of a mixture of 4-acetoxy-5-hexenoic acid and trans-6-acetoxy-4-hexenoic acid via manganese(III)-mediated oxidation of acetic acid-acetic anhydride in the presence of butadiene. Copper(II) co-catalyst enhanced the efficiency of this oxidation and copper(I) was shown to catalyze in situ conversion of the acetoxyhexenoic acids into gamma-vinyl-gamma-butyrolactone.
引用
收藏
页码:809 / 829
页数:21
相关论文
共 26 条
[1]   MANGANESE(III) COMPLEXES IN OXIDATIVE DECARBOXYLATION OF ACIDS [J].
ANDERSON, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (08) :2450-+
[2]  
BELLAMY AJ, 1981, CHEM IND-LONDON, P328
[3]   NITROMETHYLATION OF BENZENE USING ELECTROCHEMICALLY GENERATED MANGANESE(III) [J].
BELLAMY, AJ .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (03) :208-212
[4]  
BOESE AB, 1949, Patent No. 2484067
[5]   OXIDATION REACTIONS OF MANGANESE(3) ACETATE .2. FORMATION OF GAMMA-LACTONES FROM OLEFINS AND ACETIC ACID [J].
BUSH, JB ;
FINKBEIN.H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (21) :5903-&
[6]  
CLARKE R, 1975, CHEM BRIT, V11, P59
[7]   PRODUCTS AND KINETICS OF DECARBOXYLATION OF ACTIVATED AND UNACTIVATED AROMATIC CUPROUS CARBOXYLATES IN PYRIDINE AND IN QUINOLINE [J].
COHEN, T ;
BERNINGER, RW ;
WOOD, JT .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (05) :837-848
[8]  
COLEMAN JP, 1984, Patent No. 4460787
[9]  
COLEMAN JP, 1987, Patent No. 4672140
[10]  
DEKLEIN WJ, 1975, RECL TRAV CHIM PAY B, V94, P48