ELECTROCHEMICAL FLUORINATIVE ALPHA-CLEAVAGE OF CYCLIC-KETONES - SYNTHESIS OF FLUOROCARBOXYLIC ACID-ESTERS

被引：32

作者：

HARA, S

CHEN, SQ

HATAKEYAMA, T

FUKUHARA, T

SEKIGUCHI, M

YONEDA, N

机构：

[1] Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 36期

关键词：

D O I：

10.1016/0040-4039(95)01308-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electrochemical oxidation of 2,2-disubstituted cyclic ketones was carried out using Et(3)N-5HF as the electrolyte. The selective cleavage of the carbon-carbon bond between the carbonyl carbon and substituted alpha-carbon took place and fluorocarboxylic acid esters (2) were obtained in good yields after the esterification of the resulting fluoroacyl fluorides (1).

引用

收藏

页码：6511 / 6514

页数：4

相关论文

共 24 条

[1] REMOTE ANODIC SUBSTITUTION OF KETONES [J].

BECKER, JY ;

BYRD, LR ;

MILLER, LL ;

SO, YH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (04) :853-856

[2] ANODIC ALPHA-CLEAVAGE OF KETONES [J].

BECKER, JY ;

MILLER, LL ;

SIEGEL, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (04) :849-853

[3]

BENSADAT A, 1981, NOUV J CHIM, V5, P397

[4]

BENSADAT A, 1981, NOUV J CHIM, V5, P127

[5]

BENSADAT A, 1977, TETRAHEDRON LETT, V18, P3799

[6] OXIDATIVE FLUORINATION OF SULFIDES IN PRESENCE OF ET3N.3HF [J].

BRIGAUD, T ;

LAURENT, E .

TETRAHEDRON LETTERS, 1990, 31 (16) :2287-2290

[7] ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .13. SELECTIVE ANODIC ALPHA-FLUORINATION OF NITROGEN-CONTAINING HETEROCYCLIC SULFIDES AND ITS APPLICATION TO THE SYNTHESIS OF FLUORINATED FUSED HETEROCYCLES [J].

ERIAN, AW ;

KONNO, A ;

FUCHIGAMI, T .

TETRAHEDRON LETTERS, 1994, 35 (39) :7245-7248

[8] ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .4. REGIOSELECTIVE ANODIC MONOFLUORINATION OF 4-THIAZOLIDINONES AND ITS APPLICATION TO THE SYNTHESIS OF MONOFLUORO BETA-LACTAMS [J].

FUCHIGAMI, T ;

NARIZUKA, S ;

KONNO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3755-3757

[9] ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .14. ELECTROCHEMISTRY OF HYPERVALENT COMPOUNDS .2. THE FIRST ELECTROSYNTHESIS OF HYPERVALENT IODOBENZENE DIFLUORIDE DERIVATIVES AND ITS APPLICATION TO INDIRECT ANODIC GEM-DIFLUORINATION [J].

FUCHIGAMI, T ;

FUJITA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) :7190-7192

[10] ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .10. SELECTIVE ANODIC FLUORINATION OF ORGANIC TELLURIUM COMPOUNDS [J].

FUCHIGAMI, T ;

FUJITA, T ;

KONNO, A .

TETRAHEDRON LETTERS, 1994, 35 (24) :4153-4156