Anodic behaviour of aromatic oximes: an electrochemical deoximation reaction

被引：25

作者：

Bencharif, L ^{[1
]}

Tallec, A ^{[1
]}

Tardivel, R ^{[1
]}

机构：

[1] UMR CNRS,LAB ELECTROCHIM,F-35042 RENNES,FRANCE

来源：

ELECTROCHIMICA ACTA | 1997年 / 42卷 / 23-24期

关键词：

anodic oxidation; acetophenone-oximes and acetophenones; benzaldoximes; benzaldehydes and oxadiazoles; ALPHA-NITROBENZYLIC COMPOUNDS; CORRESPONDING OXIMES; OXIDATIVE CLEAVAGE; CARBONYL-COMPOUNDS; O-ACETATES; CONVERSION; REGENERATION; BENTONITE; KETOXIMES; MILD;

D O I：

10.1016/S0013-4686(97)00047-9

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

Acetophenone oximes can be converted in high yield into the corresponding ketones by controlled potential oxidation in wet acetonitrile. Whereas, on the contrary, oxidation of benzaldoximes is not selective and leads to mixtures of aldehydes and benzoic acids, together with substituted 1,2,4-oxadiazoles. (C) 1997 Elsevier Science Ltd.

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页码：3509 / 3512

页数：4

相关论文

共 18 条

[1] CARBONYL-COMPOUNDS REGENERATION WITH A MEXICAN BENTONITE [J].

ALVAREZ, C ;

CANO, AC ;

RIVERA, V ;

MARQUEZ, C .

SYNTHETIC COMMUNICATIONS, 1987, 17 (03) :279-282

[2] PREPARATIVE CONVERSION OF OXIMES TO PARENT CARBONYL COMPOUNDS BY CERIUM(4) OXIDATION [J].

BIRD, JW ;

DIAPER, DGM .

CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (01) :145-&

[3] REACTION OF OXIME O-ACETATES WITH CHROMOUS ACETATE - A METHOD FOR CONVERSION OF KETOXIMES TO KETONES UNDER MILD CONDITIONS [J].

COREY, EJ ;

RICHMAN, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (17) :5276-&

[4] ELECTROCHEMICAL CONVERSION OF ALPHA-NITROBENZYLIC COMPOUNDS INTO THE CORRESPONDING OXIMES .3. SUBSTITUENT EFFECTS [J].

MIRALLESROCH, F ;

TALLEC, A ;

TARDIVEL, R .

ELECTROCHIMICA ACTA, 1995, 40 (12) :1877-1880

[5] ELECTROCHEMICAL CONVERSION OF ALPHA-NITROBENZYLIC COMPOUNDS INTO THE CORRESPONDING OXIMES .2. MACROSCALE ELECTROLYSES [J].

MIRALLESROCH, F ;

TALLEC, A ;

TARDIVEL, R .

ELECTROCHIMICA ACTA, 1993, 38 (16) :2379-2383

[6] ELECTROCHEMICAL CONVERSION OF ALPHA-NITROBENZYLIC COMPOUNDS INTO THE CORRESPONDING OXIMES .1. ELECTROANALYTICAL INVESTIGATIONS [J].

MIRALLESROCH, F ;

TALLEC, A ;

TARDIVEL, R .

ELECTROCHIMICA ACTA, 1993, 38 (07) :963-968

[7]

MOLINA P, 1986, SYNTHESIS-STUTTGART, P843

[8] OXIDATIVE CLEAVAGE OF KETOXIMES WITH IODOSOBENZENE DIACETATE [J].

MORIARTY, RM ;

PRAKASH, O ;

VAVILIKOLANU, PR .

SYNTHETIC COMMUNICATIONS, 1986, 16 (10) :1247-1253

[9] DEOXIMATION OF OXIME O-ACETATES, OXIMES, AND OXIME ETHERS BY NONACARBONYLDIIRON OR PENTACARBONYLIRON - AN ELECTRONIC EFFECT FOR THE N-O BOND-CLEAVAGE [J].

NITTA, M ;

SASAKI, I ;

MIYANO, H ;

KOBAYASHI, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (11) :3357-3358

[10] OXIDATIVE CLEAVAGE OF ALDO AND KETO OXIMES WITH CHROMYL CHLORIDE ADSORBED ON SILICA AND BENTONITE EARTH [J].

SALMON, M ;

MIRANDA, R ;

ANGELES, E .

SYNTHETIC COMMUNICATIONS, 1986, 16 (14) :1827-1832