ELECTROCHEMICAL OXIDATIONS .4. ELECTROCHEMICAL INVESTIGATIONS INTO THE BEHAVIOR OF 2,6-DI-TERT-BUTYL-4-(4-DIMETHYLAMINOPHENYL)-PHENOL .1. PHENOL AND THE SPECIES DERIVED FROM IT - PHENOXY RADICAL, PHENOLATE ANION AND PHENOXENIUM CATION

被引:55
作者
SPEISER, B
RIEKER, A
机构
[1] Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18
关键词
D O I
10.1016/S0022-0728(79)80465-9
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
The anodic oxidation of 2,6-di-tert-butyl-4-(4-dimethylaminophenyl)phenol (IIa) was investigated by cyclic voltammetry. The stable products resulting from the oxidation are phenoxenium cation (IId) (which itself is reduced in two one-electron steps to the phenolate anion (IIc) via the phenoxy radical, IIb) and the protonated phenol (III) (which is oxidized to (IId) in a second peak at higher potential). A mechanism for the electrochemical oxidation of phenol (IIa) is suggested. © 1979 Elsevier Sequoia S.A."
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页码:373 / 395
页数:23
相关论文
共 58 条
[21]  
MUSSO H, 1967, OXIDATIVE COUPLING P, P1
[22]   THEORY OF STATIONARY ELECTRODE POLAROGRAPHY - SINGLE SCAN + CYCLIC METHODS APPLIED TO REVERSIBLE IRREVERSIBLE + KINETIC SYSTEMS [J].
NICHOLSON, RS ;
SHAIN, I .
ANALYTICAL CHEMISTRY, 1964, 36 (04) :706-&
[23]   EFFECT OF FORCED CO-PLANARITY OF BIPHENYL RINGS ON EASE OF FORMATION AND STABILITY OF PHENOLIC CATIONS [J].
NILSSON, A ;
PALMQUIST, U ;
RONLAN, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (12) :3540-3541
[24]   ANODIC-OXIDATION OF PHENOLIC COMPOUNDS .5. ANODIC METHOXYLATION OF PHENOLS - SIMPLE SYNTHESIS OF QUINONES, QUINONE ACETALS, AND 4-METHYL-ALPHA-METHOXYCYCLOHEXA-2,5-DIENONES [J].
NILSSON, A ;
PALMQUIST, U ;
PETTERSSON, T ;
RONLAN, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (07) :696-707
[25]   STABLE CARBOCATIONS .135. PROTONATION OF TRIHYDROXYBENZENES AND THEIR METHYL ETHERS IN SUPERACIDS [J].
OLAH, GA ;
MO, YK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (15) :5341-&
[26]   ROTATING-DISK ELECTRODES [J].
OPEKAR, F ;
BERAN, P .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1976, 69 (01) :1-105
[27]   ANODIC-OXIDATION OF PHENOLIC COMPOUNDS .4. SCOPE AND MECHANISM OF ANODIC INTRAMOLECULAR COUPLING OF PHENOLIC DIARYLALKANES [J].
PALMQUIST, U ;
NILSSON, A ;
PARKER, VD ;
RONLAN, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (09) :2571-2580
[28]   ANODIC-OXIDATION PATHWAYS OF PHENOLIC COMPOUNDS .2. STEPWISE ELECTRON TRANSFERS AND COUPLED HYDROXYLATIONS [J].
PAPOUCHADO, L ;
SANDFORD, RW ;
PETRIE, G ;
ADAMS, RN .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1975, 65 (01) :275-284
[29]   ON ANODIC OXIDATION OF HYDROQUINONE IN ACETONITRILE [J].
PARKER, VD ;
EBERSON, L .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (20) :1289-&
[30]  
PARKER VD, 1973, ORGANIC ELECTROCHEMI, P705