INTRAMOLECULAR CYCLIZATION OF 2'-OLEFINIC SIDE-CHAINS ON ANODICALLY OXIDIZED 4-PHENYLPHENOLS - THE EFFECT OF OLEFIN SUBSTITUENTS ON CARBON-CARBON BOND FORMATION

被引:20
作者
MORROW, GW [1 ]
CHEN, Y [1 ]
SWENTON, JS [1 ]
机构
[1] OHIO STATE UNIV,DEPT CHEM,120 W 18TH AVE,COLUMBUS,OH 43210
关键词
D O I
10.1016/S0040-4020(01)87055-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The anodic oxidation of 4-(2'-alkenylphenyl)phenols in acetonitrile/methanol affords spirodienones arising from cyclization of the olefinic side-chain to the 4-position of the phenol and reaction of the resulting benzylic cation with methanol. The efficiency of this carbon-carbon bond-forming reaction is dependent upon the olefinic substituents.
引用
收藏
页码:655 / 664
页数:10
相关论文
共 19 条
[1]   PERIODATE OXIDATION OF PHENOLS .20. REACTIONS OF 5-SUBSTITUTED 2,4-CYCLOHEXADIENONES WITH DIENOPHILES [J].
ANDERSSON, G .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (05) :403-406
[2]   PERIODATE OXIDATION OF PHENOLS .18. OXIDATION OF 2-METHOXYPHENOLS WITH PERIODIC ACID IN METHANOL [J].
ANDERSSON, G ;
BERNTSSON, P .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (09) :948-952
[3]   PERIODATE OXIDATION OF PHENOLS .19. NONDIMERIZING ORTHO-QUINOLS, ORTHO-QUINOL ETHERS, AND ORTHO-QUINONE KETALS [J].
ANDERSSON, G .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (01) :64-70
[4]  
CANNONE P, 1986, J ORG CHEM, V51, P2148
[5]   SYNTHETICALLY AND BIOLOGICALLY INTERESTING N-ACYLQUINONE IMINE KETALS AND N-ACYLQUINOL IMINE ETHERS FROM ANODIC-OXIDATION OF ANILIDES [J].
CHEN, CP ;
CHOU, CT ;
SWENTON, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :946-948
[6]   A CONVERGENT STRATEGY FOR SYNTHESIS OF ERYTHRINA ALKALOIDS [J].
CHOU, CT ;
SWENTON, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (22) :6898-6899
[7]   ANODIC-OXIDATION OF 1,4-DIMETHOXY AROMATIC-COMPOUNDS - FACILE ROUTE TO FUNCTIONALIZED QUINONE BISKETALS [J].
HENTON, DR ;
MCCREERY, RL ;
SWENTON, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (03) :369-378
[8]  
HENTON DR, 1980, J ORG CHEM, V45, P3422, DOI 10.1021/jo01305a010
[9]  
LAMBERT JB, 1967, INTRO ORGANIC SPECTR, P93
[10]   SPIRO-ANNULATED CYCLOHEXA-2,5-DIENONES VIA ELECTROOXIDATION OF P-ARYL PHENOLS A NOVEL MODE OF ANODIC CARBON-CARBON BOND FORMATION [J].
MORROW, GW ;
SWENTON, JS .
TETRAHEDRON LETTERS, 1987, 28 (45) :5445-5448