ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .12. SELECTIVE ANODIC MONOFLUORINATION OF FLUOROALKYL AND ALKYL SULFIDES

被引：73

作者：

FUCHIGAMI, T

KONNO, A

NAKAGAWA, K

SHIMOJO, M

机构：

[1] Department of Electronic Chemistry, Tokyo Institute of Technology, Yokohama 227, Nagatsuta, Midori-ku

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 20期

关键词：

D O I：

10.1021/jo00099a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly regioselective anodic monofluorination of various aryl and alkyl fluoroalkyl sulfides was successfully carried out, and fluorine was exclusively (aryl sulfides) or preferentially (alkyl sulfides) introduced at the position alpha to the fluoroalkyl group. Even simple alkyl phenyl sulfides devoid of an electron-withdrawing group could be anodically monofluorinated in satisfactory yields for the first time when etheral solvents were used as an electrolytic solution. A unique Pummerer-type mechanism uta fluorosulfonium ions was proposed for this anodic fluorination by comparison with anodic alpha-methoxylation previously studied.

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页码：5937 / 5941

页数：5

相关论文

共 33 条

[1] INTRAMOLECULAR FRIEDEL-CRAFTS ALKYLATION AND CHLOROALKYLATION OF 5-ARYL-1,1,1-TRIFLUOROPENTAN-2-ONES - A ROUTE TO (TRIFLUOROMETHYL)DIHYDRONAPHTHALENES AND (TRIFLUOROMETHYL)TETRAHYDRONAPHTHALENES [J].

BONNETDELPON, D ;

CHARPENTIERMORIZE, M ;

JACQUOT, R .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (04) :759-762

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

BRIGAUD, T ;

LAURENT, E .

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

[3]

CHILDS WV, 1991, ORGANIC ELECTROCHEMI, pCH26

[4]

Filler R., 1982, BIOMEDICAL ASPECTS F

[5] ELECTROLYTIC TRANSFORMATION OF FUNCTIONAL-GROUPS OF FLUOROORGANIC COMPOUNDS .1. ANODIC METHOXYLATION AND ACETOXYLATION OF TRIFLUOROETHYL SULFIDE [J].

FUCHIGAMI, T ;

NAKAGAWA, Y ;

NONAKA, T .

TETRAHEDRON LETTERS, 1986, 27 (33) :3869-3872

[6] FLUORIDE-ION PROMOTED ANODIC SUBSTITUTIONS OF CHALCOGENO COMPOUNDS .1. REGIOSELECTIVE ANODIC ALKOXYLATION OF SULFIDES [J].

FUCHIGAMI, T ;

YANO, H ;

KONNO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6731-6733

[7] ELECTROLYTIC REACTIONS OF FLUORO ORGANIC-COMPOUNDS .8. FURTHER STUDY ON ANODIC METHOXYLATION AND ACETOXYLATION OF ARYL FLUOROALKYL SULFIDES [J].

FUCHIGAMI, T ;

YAMAMOTO, K ;

KONNO, A .

TETRAHEDRON, 1991, 47 (4-5) :625-634

[8] ELECTROCHEMICAL GENERATION OF REACTIVE NITROGEN SPECIES .11. ELECTROLYTIC TRANSFORMATION OF FLUOROORGANIC COMPOUNDS .3. HIGHLY REGIOSELECTIVE ANODIC METHOXYLATION OF N-(2,2,2-TRIFLUOROETHYL)AMINES [J].

FUCHIGAMI, T ;

NAKAGAWA, Y ;

NONAKA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5489-5491

[9] ELECTROLYTIC REACTIONS OF FLUORO ORGANIC-COMPOUNDS .7. ANODIC METHOXYLATION AND ACETOXYLATION OF 2,2,2-TRIFLUOROETHYL SULFIDES - PREPARATION OF HIGHLY USEFUL TRIFLUOROMETHYLATED BUILDING-BLOCKS [J].

FUCHIGAMI, T ;

YAMAMOTO, K ;

NAKAGAWA, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :137-142

[10] ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .1. REGIOSELECTIVE ANODIC MONOFLUORINATION OF ORGANOSULFUR COMPOUNDS [J].

FUCHIGAMI, T ;

SHIMOJO, M ;

KONNO, A ;

NAKAGAWA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6074-6075

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