ANODIC-OXIDATION OF METHYLBENZENES - SYNTHETIC ROUTES TO CERTAIN CYCLOHEXA-1,4-DIENES

被引:6
作者
BARBA, I
CHINCHILLA, R
GOMEZ, C
机构
[1] Departamento de Quimica Orgánica, Universidad de Alicante, 03080-Alicante
关键词
D O I
10.1021/jo00011a042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The anodic methoxylation of a series of methylbenzenes (mesitylene, pseudocumene, hemimellitene, pentamethylbenzene, and hexamethylbenzene) afforded chain methoxylated products as well as nuclear-addition products. For nuclear-addition products both cis/trans isomers are possible. In the cyclohexa-1,4-dienes obtained from these substrates the cis/trans ratio found is different. A probable mechanism is provided.
引用
收藏
页码:3673 / 3676
页数:4
相关论文
共 21 条
[1]  
ALONSO F, 1990, TETRAHEDRON, V46, P2096
[2]  
BARBA F, 1986, J CHEM RES-S, P228
[3]   ELECTROCHEMICAL OBTENTION OF CIS-3,6-DIMETHOXY-3,6-DIMETHYL-1,4-CYCLOHEXADIENE AND TRANS-3,6-DIMETHOXY-3,6-DIMETHYL-1,4-CYCLOHEXADIENE [J].
BARBA, F ;
GUIRADO, A ;
BARBA, I .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (16) :3022-3024
[4]   ELECTROCHEMICAL METHOXYLATIONS OF SIDE-CHAIN METHOXYLATED PARA-XYLENE DERIVATIVES [J].
BARBA, F ;
GUIRADO, A ;
BARBA, I .
ELECTROCHIMICA ACTA, 1984, 29 (12) :1639-1641
[5]   ANODIC-OXIDATION OF ALKYLATED BIPHENYLS - SYNTHETIC ROUTES TO CERTAIN CYCLOHEXA-1,4-DIENES [J].
BARBA, I ;
CHINCHILLA, R ;
GOMEZ, C .
TETRAHEDRON LETTERS, 1989, 30 (24) :3187-3188
[6]   CIS-CYCLOHEXA-1, 4-DIENE AND TRANS-CYCLOHEXA-1,4-DIENE DERIVATIVES - AMMONIA AND METHANE CHEMICAL IONIZATION MASS-SPECTROMETRY [J].
BARBA, I ;
ALONSO, F ;
CHINCHILLA, R ;
GOMEZ, C .
ORGANIC MASS SPECTROMETRY, 1989, 24 (11) :1029-1030
[7]   STEREOSELECTIVE OBTENTION OF TRANS-3,6-DIMETHOXY-1,3,6-TRIMETHYLCYCLOHEXA-1,4-DIENE BY ANODIC METHOXYLATION OF PSEUDOCUMENE [J].
BARBA, I ;
GOMEZ, C ;
CHINCHILLA, R .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3272-3273
[8]   ANODIC-OXIDATION OF XYLENES - ELECTROCHEMICAL OBTENTION OF CYCLOHEXA-1,4-DIENE DERIVATIVES [J].
BARBA, I ;
ALONSO, F ;
FLORENCIO, F .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) :4365-4367
[9]  
BARBA I, 1988, CHEM SCRIPTA, V28, P419
[10]  
BARBA I, IN PRESS TETRAHEDRON