TETRABUTYLAMMONIUM DIFLUOROTRIPHENYLSTANNATE AS A NEW ANHYDROUS SYNTHETIC EQUIVALENT TO TBAF

被引：94

作者：

GINGRAS, M ^{[1
]}

机构：

[1] MCGILL UNIV,DEPT CHEM,MONTREAL H3A 2K6,QUEBEC,CANADA

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 50期

关键词：

D O I：

10.1016/0040-4039(91)80112-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrabutylammonium difluorotriphenylstannate (1) is the first hypervalent complex of tin acting as a fluorinating agent. In contrast to TBAF and TASF, this crystalline complex is relatively stable up to 210-degrees-C and is not hygroscopic or hydrated. Enolsilylether alkylations with alkyl bromides proceeded in good to quantitative yields in the presence of (1), which was kept for years unprotected from moisture. Relative rate studies indicated that nucleophilic fluorination of benzyl bromide proceeded 18 times faster than with dried cesium fluoride in refluxing CH3CN.

引用

收藏

页码：7381 / 7384

页数：4

相关论文

共 29 条

[1]

ARJUN CS, 1980, J ORGANOMET CHEM, V197, P181

[2]

BENSOAM J, 1979, TETRAHEDRON LETT, P353

[3] TETRABUTYLAMMONIUM BIFLUORIDE - A VERSATILE AND EFFICIENT FLUORINATING AGENT [J].

BOSCH, P ;

CAMPS, F ;

CHAMORRO, E ;

GASOL, V ;

GUERRERO, A .

TETRAHEDRON LETTERS, 1987, 28 (40) :4733-4736

[4] A RAPID AND EFFICIENT METHOD FOR THE FLUOROALKYLATION OF AMINES AND AMIDES - DEVELOPMENT OF A METHOD SUITABLE FOR INCORPORATION OF THE SHORT-LIVED POSITRON EMITTING RADIONUCLIDE F-18 [J].

CHI, DY ;

KILBOURN, MR ;

KATZENELLENBOGEN, JA ;

WELCH, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04) :658-664

[5] SYNTHESES, PROPERTIES, AND STRUCTURES OF ANHYDROUS TETRAMETHYLAMMONIUM FLUORIDE AND ITS 1-1 ADDUCT WITH TRANS-3-AMINO-2-BUTENENITRILE [J].

CHRISTE, KO ;

WILSON, WW ;

WILSON, RD ;

BAU, R ;

FENG, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) :7619-7625

[6] DRIFLUOR REAGENTS - NON-HYGROSCOPIC SOURCES OF FLUORIDE-ION [J].

CLARK, JH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (18) :789-791

[7] FLUORIDE-ION AS A BASE IN ORGANIC-SYNTHESIS [J].

CLARK, JH .

CHEMICAL REVIEWS, 1980, 80 (05) :429-452

[8] THE SYNTHESIS OF ORGANOFLUORINE COMPOUNDS USING POTASSIUM FLUORIDE-TETRAPHENYLPHOSPHONIUM BROMIDE SYSTEMS [J].

CLARK, JH ;

MACQUARRIE, DJ .

TETRAHEDRON LETTERS, 1987, 28 (01) :111-114

[9] CALCIUM FLUORIDE-SUPPORTED ALKALI-METAL FLUORIDES - NEW REAGENTS FOR NUCLEOPHILIC FLUORINE TRANSFER-REACTIONS [J].

CLARK, JH ;

HYDE, AJ ;

SMITH, DK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) :791-793

[10] ANHYDROUS TETRABUTYLAMMONIUM FLUORIDE - A MILD BUT HIGHLY EFFICIENT SOURCE OF NUCLEOPHILIC FLUORIDE-ION [J].

COX, DP ;

TERPINSKI, J ;

LAWRYNOWICZ, W .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) :3216-3219