ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .15. STEREOCHEMICAL STUDY OF THE ANODIC MONOFLUORINATION OF ALPHA-PHENYLSULFENYL ACETATES

被引：25

作者：

NARIZUKA, S ^{[1
]}

KOSHIYAMA, H ^{[1
]}

KONNO, A ^{[1
]}

FUCHIGAMI, T ^{[1
]}

机构：

[1] TOKYO INST TECHNOL,DEPT ELECTR CHEM,MIDORI KU,YOKOHAMA,KANAGAWA 226,JAPAN

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1995年 / 73卷 / 01期

关键词：

ELECTROLYTIC PARTIAL FLUORINATION; ORGANIC COMPOUNDS; ALPHA-PHENYLSULFENYL ACETATES; DIASTEREOSELECTIVITY; CHIRAL FLUOROCOMPOUNDS;

D O I：

10.1016/0022-1139(94)03207-G

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The diastereoselective anodic fluorination of alpha-phenylsulfenyl esters by intramolecular asymmetry-induction has been studied using chiral auxiliaries such as phenethyl, bornyl, isobornyl, menthyl and 8-phenylmenthyl groups. Of these chiral auxiliaries, the 8-phenylmenthyl group gave the best diastereoselectivity. The diastereoselectivity was also affected by supporting electrolytes and it was found that Et(4)NF . 3HF showed better selectivity in comparison to Et(3)N . 3HF and Et(3)N . 2HF.

引用

页码：121 / 127

页数：7

共 30 条

[11]

KANEKO T, 1979, TETRAHEDRON LETT, P103

[12]

KONNO A, 1995, J APPL ELECTROCHEM, V25, P173

[13] NEW MECHANISTIC ASPECTS OF ANODIC MONOFLUORINATION OF HALOGENOALKYL AND ALKYL PHENYL SULFIDES [J].

KONNO, A ;

NAKAGAWA, K ;

FUCHIGAMI, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (15) :1027-1029

[14] NEW PREPARATION OF ALPHA-FLUORO OR ALPHA,ALPHA-DIFLUORO BENZYLIC KETONES, ESTER AND NITRILE [J].

LAURENT, E ;

MARQUET, B ;

TARDIVEL, R ;

THIEBAULT, H .

TETRAHEDRON LETTERS, 1987, 28 (21) :2359-2362

[15] REGIOSELECTIVITY IN ANODIC FLUORIDATION OF BENZYL DERIVATIVES [J].

LAURENT, E ;

MARQUET, B ;

TARDIVEL, R .

TETRAHEDRON, 1991, 47 (24) :3969-3980

[16] ELECTROCHEMICAL MONOFLUORINATION AND DIFLUORINATION OF BENZYL-GROUPS [J].

LAURENT, E ;

MARQUET, B ;

TARDIVEL, R .

TETRAHEDRON, 1989, 45 (14) :4431-4444

[17] BENZYL-POSITION ELECTROFLUORINATION IN SULFOLANE [J].

LAURENT, E ;

MARQUET, B ;

TARDIVEL, R .

JOURNAL OF FLUORINE CHEMISTRY, 1990, 49 (01) :115-126

[18] REACTION OF XENON DIFLUORIDE .3. OXIDATIVE-FLUORINATION AND ALPHA-FLUORINATION OF SULFUR(II) COMPOUNDS [J].

MARAT, RK ;

JANZEN, AF .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (16) :3031-3034

[19]

MCCARTHY JR, 1988, J AM CHEM SOC, V28, P3674

[20] ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .8. HIGHLY REGIOSELECTIVE ANODIC MONOFLUORINATION OF BETA-LACTAMS [J].

NARIZUKA, S ;

FUCHIGAMI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4200-4201

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