SYNTHESIS OF (Z)-1,2-DIHALO-1-ALKENES BY THE REACTION OF (Z)-(BETA-HALOVINYL)PHENYLIODONIUM SALTS WITH N-BU4NX OR KX/CUX - COMPETITIONS BETWEEN NUCLEOPHILIC VINYLIC SUBSTITUTIONS AND AROMATIC SUBSTITUTIONS

被引：37

作者：

OCHIAI, M ^{[1
]}

OSHIMA, K ^{[1
]}

MASAKI, Y ^{[1
]}

机构：

[1] GIFU PHARMACEUT UNIV, GIFU 502, JAPAN

来源：

CHEMISTRY LETTERS | 1994年 / 05期

关键词：

D O I：

10.1246/cl.1994.871

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nucleophilic vinylic substitutions of (Z)-(beta-halovinyl)phenyliodonium salts with tetrabutylammonium halides proceed in a stereoselective manner with retention of configuration yielding vicinal (Z)-vinyl dihalides. This reaction competes with nucleophilic aromatic substitutions. Similar competition was observed in the reactions with potassium halides/cuprous halides.

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页码：871 / 874

页数：4

相关论文

共 23 条

[1] ELECTROPHILIC ADDITIONS OF POSITIVE IODINE TO ALKYNES THROUGH AN IODONIUM MECHANISM [J].

BARLUENGA, J ;

RODRIGUEZ, MA ;

CAMPOS, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3104-3106

[2] THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS .7. THE POSSIBLE ROLE OF RADICAL MECHANISMS IN THE PHENYLATION PROCESS FOR BISMUTH(V), AND RELATED LEAD(IV), IODINE(III), AND ANTIMONY(V) REAGENTS [J].

BARTON, DHR ;

FINET, JP ;

GIANNOTTI, C ;

HALLEY, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :241-249

[3] DIARYLIODONIUM SALTS .17. PHENYLATION OF 1,3-INDANDIONES [J].

BERINGER, FM ;

HUANG, SJ ;

GALTON, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (14) :2819-&

[4] DIARYLIODONIUM SALTS .2. THE PHENYLATION OF ORGANIC AND INORGANIC BASES [J].

BERINGER, FM ;

BRIERLEY, A ;

DREXLER, M ;

GINDLER, EM ;

LUMPKIN, CC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (11) :2708-2712

[5] DIRECT AND REGIOCONTROLLED SYNTHESIS OF ALPHA-PHENYL KETONES FROM SILYL ENOL ETHERS AND DIPHENYLIODONIUM FLUORIDE [J].

CHEN, KC ;

KOSER, GF .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5764-5767

[6] EXTREMELY FACILE LIGAND-EXCHANGE AND DISPROPORTIONATION REACTIONS OF DIARYL SULFOXIDES, SELENOXIDES, AND TRIARYLPHOSPHINE OXIDES WITH ORGANOLITHIUM AND GRIGNARD-REAGENTS [J].

FURUKAWA, N ;

OGAWA, S ;

MATSUMURA, K ;

FUJIHARA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6341-6348

[7]

HARA S, 1983, SYNTHESIS-STUTTGART, P1005

[8] DIALKYLCARBAMOYL(DIARYL)IODANES [J].

KOTALI, E ;

VARVOGLIS, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2759-2763

[9] STEREOSELECTION IN NUCLEOPHILIC-SUBSTITUTION AT AN SP2 CARBON [J].

MILLER, SI .

TETRAHEDRON, 1977, 33 (10) :1211-1218

[10] REACTIONS OF NUCLEOPHILES WITH ETHYLENIC SUBSTRATES [J].

MODENA, G .

ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (02) :73-&