Two-electron phenolic oxidations using phenyliodonium dicarboxylates

被引:94
作者
Pelter, A [1 ]
Ward, RS [1 ]
机构
[1] Univ Coll Swansea, Dept Chem, Swansea SA2 8PP, W Glam, Wales
关键词
phenol oxidation; phenyliodonium dicarboxylates; cyclohexadienones; cyclisations;
D O I
10.1016/S0040-4020(00)00935-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phenolic oxidations by PhI(OCOR)(2) are reviewed. Consideration is given to the mechanisms of the reactions and to the differing consequences of inter- and intra-molecular nucleophilic attack on the intermediate phenyloxenium ions. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:273 / 282
页数:10
相关论文
共 79 条
[1]   REACTION OF PYRIDINE 1-OXIDES AND N-IMINOPYRIDINIUM YLIDES WITH DIAZONIUM SALTS N-ARYLOXYPYRIDINIUM SALTS AND THEIR BASE-CATALYZED REARRANGEMENT [J].
ABRAMOVITCH, RA ;
INBASEKARAN, MN ;
KATO, S ;
SINGER, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (10) :1717-1724
[2]   ARYLOXENIUM IONS - GENERATION FROM N-(ARYLOXY)PYRIDINIUM TETRAFLUOROBORATES AND REACTION WITH ANISOLE AND BENZONITRILE [J].
ABRAMOVITCH, RA ;
ALVERNHE, G ;
BARTNIK, R ;
DASSANAYAKE, NL ;
INBASEKARAN, MN ;
KATO, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) :4558-4565
[3]   CHEMISTRY OF STABLE PHONOXY RADICALS [J].
ALTWICKE.ER .
CHEMICAL REVIEWS, 1967, 67 (05) :475-+
[4]   Reaction of masked o-benzoquinones towards dienophiles with inverse electronic demand.: Enol and thioenol ethers as dienophiles [J].
Arjona, O ;
Medel, R ;
Plumet, J .
TETRAHEDRON LETTERS, 1999, 40 (48) :8431-8433
[5]   ORGANIC POLYVALENT IODINE COMPOUNDS [J].
BANKS, DF .
CHEMICAL REVIEWS, 1966, 66 (03) :243-&
[6]   SYNTHESIS OF QUINONE-IMINES WITH IODOXYBENZENE [J].
BARRET, R ;
DAUDON, M .
SYNTHETIC COMMUNICATIONS, 1990, 20 (10) :1543-1549
[7]   OXIDATION OF PHENOLS TO QUINONES BY BIS(TRIFLUOROACETOXY)IODOBENZENE [J].
BARRET, R ;
DAUDON, M .
TETRAHEDRON LETTERS, 1990, 31 (34) :4871-4872
[8]   CONSTITUENTS OF EUPOMATIA SPECIES .11. NEW EUPODIENONE LIGNANS FROM THE FLOWERS OF EUPOMATIA-LAURINA [J].
CARROLL, AR ;
TAYLOR, WC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (11) :1871-1879
[9]   STABILE PHENOXY-KATIONEN AUS ARYLIERTEN PHENOLEN [J].
DIMROTH, K ;
UMBACH, W ;
THOMAS, H .
CHEMISCHE BERICHTE-RECUEIL, 1967, 100 (01) :132-&
[10]   NOVEL PHENOL-BENZENE C-C COUPLING REACTION - ACID-CATALYZED REACTION OF N-ACYL-O-ARYLHYDROXYLAMINES WITH BENZENES [J].
ENDO, Y ;
SHUDO, K ;
OKAMOTO, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (23) :7721-7723