INTRAMOLECULAR AROMATIC-SUBSTITUTION WITH BISTHIOCARBOCATIONS - VARIATIONS OF LEWIS ACID, SOLVENT AND ORTHOTHIO SUBSTITUENTS

被引：5

作者：

GAMAGE, SA ^{[1
]}

SMITH, RAJ ^{[1
]}

机构：

[1] UNIV OTAGO,DEPT CHEM,POB 56,DUNEDIN,NEW ZEALAND

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1990年 / 43卷 / 05期

关键词：

D O I：

10.1071/CH9900815

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The effects of Lewis acid, solvent and orthothio substituent have been examined with regard to intramolecular electrophilic aromatic substitution (annulation) with bisthiocarbocations. A suspension of silver trifluoromethanesulfonate in dichloromethane, creating bis(arylthio)carbocations, was found to be the most effective for annulation of six-membered rings. © 1990 ASEG.

引用

收藏

页码：815 / 824

页数：10

相关论文

共 20 条

[1] COMPLEXES OF MOLYBDENUM-(II) AND MOLYBDENUM-(IV) AND TUNGSTEN(II) WITH STERICALLY HINDERED THIOLATE LIGANDS - SYNTHESIS, REACTIVITY, AND X-RAY CRYSTAL-STRUCTURES OF [PPH4] [MO(SC6H2PRI3-2,4,6)3(CO)2] AND [MO(NNPH)(SC6H2PRI3-2,4,6)3(NCME)] [J].

BLOWER, PJ ;

DILWORTH, JR ;

HUTCHINSON, J ;

NICHOLSON, T ;

ZUBIETA, JA .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1985, (12) :2639-2645

[2] GENERATION OF 2-LITHIO-2-(METHYLTHIO)-1,3-BENZODITHIOLES, NEW CARBOXYL CARBANION EQUIVALENTS, AND THEIR APPLICATION TO THE SYNTHESES OF UNSYMMETRICAL HEXATHIOORTHOOXALATES [J].

BROWN, CA ;

MILLER, RD ;

LINDSAY, CM ;

SMITH, K .

TETRAHEDRON LETTERS, 1984, 25 (09) :991-994

[3]

COLSMAN MR, 1988, J AM CHEM SOC, V110, P6866

[4] OXAZIRIDINE-SILVER FLUOBORATE COMPLEXES - SITE OF COMPLEXATION BY C-13 NUCLEAR MAGNETIC-RESONANCE AND X-RAY PHOTOELECTRON-SPECTROSCOPY [J].

CRIST, DR ;

JORDAN, GJ ;

HASHMALL, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (15) :4927-4932

[5] THE S,S-ACETAL TO CARBONYL TRANSFORMATION USING THE SOFT NO+ OR CL+ SPECIES [J].

ELWASSIMY, MTM ;

JORGENSEN, KA ;

LAWESSON, SO .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (09) :2201-2203

[6]

FUJI K, 1978, TETRAHEDRON LETT, P3561

[7] SOLVENT EFFECTS ON REACTIVITIES OF ORGANOMETALLIC COMPOUNDS [J].

GUTMANN, V .

COORDINATION CHEMISTRY REVIEWS, 1976, 18 (02) :225-255

[8]

KENG GS, 1977, THESIS U OTAGO

[9] NOVEL ONE-STEP SYNTHESIS OF EPOXIDES FROM BETA-HYDROXY-SELENIDES AND SULFIDES [J].

LABOUREUR, JL ;

DUMONT, W ;

KRIEF, A .

TETRAHEDRON LETTERS, 1984, 25 (40) :4569-4572

[10]

MANAS AR, 1987, TETRAHEDRON, V43, P1847