Observations on the reactivity of pentafluorophenyl sulfonate esters

被引：28

作者：

Caddick, S

Wilden, JD

Judd, DB

机构：

[1] UCL, Dept Chem, London WC1H 0AJ, England

[2] GlaxoSmithKline, Harlow CM19 5AW, Essex, England

来源：

CHEMICAL COMMUNICATIONS | 2005年 / 21期

关键词：

D O I：

10.1039/b501212k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Studies on displacement reactions of alkyl pentafluorophenyl (PFP) sulfonates with amines are consistent with a mechanism involving an elimination-addition pathway; comparisons between the reactivity of PFP-sulfonates with sulfonyl chlorides and PFP-sulfonates with PFP-esters are also presented.

引用

收藏

页码：2727 / 2728

页数：2

相关论文

共 17 条

[1] Direct synthesis of sulfonamides and activated sulfonate esters from sulfonic acids [J].

Caddick, S ;

Wilden, JD ;

Judd, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (04) :1024-1025

[2] A new route to sulfonamides via intermolecular radical addition to pentafluorophenyl vinylsulfonate and subsequent aminolysis [J].

Caddick, S ;

Wilden, JD ;

Bush, HD ;

Wadman, SN ;

Judd, DB .

ORGANIC LETTERS, 2002, 4 (15) :2549-2551

[3] SULFONYL TRANSFER-REACTIONS [J].

GORDON, IM ;

MASKILL, H ;

RUASSE, MF .

CHEMICAL SOCIETY REVIEWS, 1989, 18 (02) :123-151

[4] Recent advances in the synthesis, design and selection of cysteine protease inhibitors [J].

Hernandez, AA ;

Roush, WR .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2002, 6 (04) :459-465

[5] SONOCHEMISTRY - ORGANIC-SYNTHESIS UNDER ULTRASONIC IRRADIATION [J].

KIMURA, T ;

ANDO, T .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1988, 46 (12) :1124-1133

[6] ORGANIC SULFUR MECHANISMS .35. MECHANISMS OF HYDROLYSIS AND RELATED NUCLEOPHILIC DISPLACEMENT-REACTIONS OF ALKANESULFONYL CHLORIDES - PH-DEPENDENCE AND THE MECHANISM OF HYDRATION OF SULFENES [J].

KING, JF ;

LAM, JYL ;

SKONIECZNY, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1743-1749

[7]

KISFALUDY L, 1973, LIEBIGS ANN CHEM, P1421

[8] SYNTHESIS OF N-CARBOBENZOXYAMINO ACID AND PEPTIDE PENTAFLUOROPHENYL ESTERS AS INTERMEDIATES IN PEPTIDE SYNTHESIS [J].

KISFALUDY, L ;

ROBERTS, JE ;

JOHNSON, RH ;

MAYERS, GL ;

KOVACS, J .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10) :3563-+

[9]

KISFALUDY L, 1983, SYNTHESIS-STUTTGART, P325

[10]

LYASHCHUCK SN, 1993, J CHEM SOC P2, V6, P1153