CONJUGATE REDUCTION OF QUINONE DERIVATIVES - A ROUTE TO PHENOL KETO-TAUTOMER EQUIVALENTS

被引:13
作者
DOTY, BJ [1 ]
MORROW, GW [1 ]
机构
[1] UNIV DAYTON, DEPT CHEM, DAYTON, OH 45469 USA
关键词
D O I
10.1016/S0040-4039(00)97004-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,4-addition of hydride to quinone monoketals 1 and p-quinol ethers 2, mediated by bis-(2,6-di-t-butyl-4-methylphenoxy)-methylaluminum (MAD), affords 4,4-substituted-2-cyclohexen-1-ones 3, which represent keto-tautomer equivalents of phenols. © 1990.
引用
收藏
页码:6125 / 6128
页数:4
相关论文
共 10 条
[1]  
HENTON DR, 1980, J ORG CHEM, V45, P3422, DOI 10.1021/jo01305a010
[2]  
KOENIG TM, 1990, TETRAHEDRON LETT, P3237
[3]  
LIPSHUTZ BH, 1989, SYNLETT, V1, P64
[4]   AMPHIPHILIC REACTIONS BY MEANS OF EXCEPTIONALLY BULKY ORGANO-ALUMINUM REAGENTS - RATIONAL APPROACH FOR OBTAINING UNUSUAL EQUATORIAL, ANTI-CRAM, AND 1,4 SELECTIVITY IN CARBONYL ALKYLATION [J].
MARUOKA, K ;
ITOH, T ;
SAKURAI, M ;
NONOSHITA, K ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3588-3597
[5]   UNUSUAL CONJUGATE ADDITION OF ORGANOLITHIUM REAGENT TO ALPHA,BETA-UNSATURATED KETONE [J].
MARUOKA, K ;
NONOSHITA, K ;
YAMAMOTO, H .
TETRAHEDRON LETTERS, 1987, 28 (46) :5723-5726
[6]  
RONLAN A, 1978, J CHEM SOC P1, P696
[7]  
SHAH RD, 1988, J AM CHEM SOC, V110, P3702
[8]   OXYGENOPHILIC ORGANOALUMINUM-MEDIATED CONJUGATE ADDITION OF ALKYLLITHIUM AND GRIGNARD-REAGENTS TO QUINONE MONOKETALS AND QUINOL ETHERS - THE DIRECTING EFFECT OF A METHOXY GROUP ON THE 1,4-ADDITION PROCESS [J].
STERN, AJ ;
ROHDE, JJ ;
SWENTON, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) :4413-4419
[9]  
Swenton J. S., 1988, CHEM QUINONOID COM 2, V2, P899