CONTROLLED OXIDATION OF ENOLATES TO ALPHA-CARBONYL RADICALS AND ALPHA-CARBONYL CATIONS

被引：43

作者：

ROCK, M ^{[1
]}

SCHMITTEL, M ^{[1
]}

机构：

[1] UNIV FREIBURG,INST ORGAN CHEM & BIOCHEM,ALBERTSTR 21,D-79104 FREIBURG,GERMANY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 23期

关键词：

D O I：

10.1039/c39930001739

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Depending on the oxidation strength of the one-electron oxidants either persistent alpha-carbonyl radicals or a-carbonyl cation derived benzofurans are formed from enolates A1-A6, a result which can readily be rationalized by the measured oxidation potentials of enolates A1-A6 and alpha-carbonyl radicals R1-R6.

引用

页码：1739 / 1741

页数：3

共 35 条

[1] SUBSTITUENT EFFECT ON THE ELECTROCHEMICAL OXIDATION OF TRITYL ANIONS
BANK, S
EHRLICH, CL
ZUBIETA, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (09) : 1454 - 1458
[2] ACIDITIES AND HOMOLYTIC BOND-DISSOCIATION ENERGIES (BDES) OF BENZYL-TYPE C-H BONDS IN STERICALLY CONGESTED SUBSTRATES
BORDWELL, FG
CHENG, JP
SATISH, AV
TWYMAN, CL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) : 6542 - 6546
[3] THERMODYNAMIC DETERMINATION OF PKAS OF WEAK HYDROCARBON ACIDS USING ELECTROCHEMICAL REDUCTION DATA - TRIARYLMETHYL ANIONS, CYCLOHEPTATRIENYL ANION, AND TRIPHENYL CYCLOPROPENYL AND TRIALKYLCYCLOPROPENYL ANIONS
BRESLOW, R
CHU, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) : 411 - 418
[4] PKA OF TRIPHENYLCYCLOPROPENE . ELECTROCHEMICAL DETERMINATION OF AN INACCESSIBLE EQUILIBRIUM CONSTANT
BRESLOW, R
BALASUBR.K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (18) : 5182 - &
[5] ELECTROCHEMICAL DETERMINATION OF PKR+ FOR SOME ANTIAROMATIC CYCLOPENTADIENYL CATIONS
BRESLOW, R
MAZUR, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) : 584 - 585
[6] HYDRIDE AFFINITIES OF CARBENIUM IONS IN ACETONITRILE AND DIMETHYL-SULFOXIDE SOLUTION
CHENG, JP
HANDOO, KL
PARKER, VD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) : 2655 - 2660
[7] RELATIVELY STABLE N-BENZHYDRYLKETENE AND N-BENZYLDIARYLKETENE IMINES AND THEIR CONVERSION TO CYANODIARYLMETHANES VIA AN ISOLABLE RADICAL
CLARKE, LF
HEGARTY, AF
ONEILL, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) : 362 - 366
[8] ELECTRONEGATIVELY SUBSTITUTED CARBOCATIONS
CREARY, X
[J]. CHEMICAL REVIEWS, 1991, 91 (08) : 1625 - 1678
[9] CREARY X, 1989, ADV CARBOCATION CHEM, V1, P45
[10] CARBONIUM IONS .1. AN ACIDITY FUNCTION (CO) DERIVED FROM ARYLCARBONIUM ION EQUILIBRIA
DENO, NC
JARUZELSKI, JJ
SCHRIESHEIM, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (11) : 3044 - 3051

← 1 2 3 4 →