Design and reactivity of organic functional groups - Preparation and nucleophilic displacement reactions of imidazole-1-sulfonates (imidazylates)

被引：35

作者：

Vatele, JM ^{[1
]}

Hanessian, S ^{[1
]}

机构：

[1] UNIV MONTREAL,DEPT CHEM,MONTREAL,PQ H3C 3J7,CANADA

来源：

TETRAHEDRON | 1996年 / 52卷 / 32期

关键词：

S(N)2 displacement; imidazole-1-sulfonate group;

D O I：

10.1016/0040-4020(96)00586-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imidazole-1-sulfonate, a new type of leaving group by remote activation, allows facile S(N)2 substitution reactions at sterically crowded centers with various nucleophiles under mild conditions. It could be easily prepared from alcohols with cheap reagents in quantitative yield. Copyright (C) 1996 Elsevier Science Ltd

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页码：10557 / 10568

页数：12

相关论文

共 52 条

[1] THE HEX-5-ENOSE DEGRADATION - ZINC DUST CLEAVAGE OF 6-DEOXY-6-IODO-ALPHA-D-GALACTOPYRANOSIDIC LINKAGES IN METHYLATED DISACCHARIDES AND TRISACCHARIDES [J].

ASPINALL, GO ;

CHATTERJEE, D ;

KHONDO, L .

CANADIAN JOURNAL OF CHEMISTRY, 1984, 62 (12) :2728-2735

[2]

BENTLEY JW, 1991, CHEM SULFONIC ACIDS, pCH16

[3] THE CONFORMATION OF 8-MEMBERED 3,2'-O-ISOPROPYLIDENE ACETALS OF SOME COMMON DISACCHARIDES [J].

BERNABE, M ;

FERNANDEZMAYORALAS, A ;

JIMENEZBARBERO, J ;

MARTINLOMAS, M ;

RIVERA, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (11) :1867-1873

[4] SYNTHESIS OF DEOXYHALOGENO SUGARS - DISPLACEMENT OF THE (TRIFLUOROMETHANESULFONYL)OXY (TRIFLYL) GROUP BY HALIDE ION [J].

BINKLEY, RW ;

AMBROSE, MG ;

HEHEMANN, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (22) :4387-4391

[5]

BOCK K, 1984, ACTA CHEM SCAND, P255

[6] USE OF TETRABUTYLAMMONIUM AZIDE IN CURTIUS REARRANGEMENT [J].

BRANDSTROM, A ;

LAMM, B ;

PALMERTZ, I .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1974, B 28 (06) :699-701

[7] NEW HALOGENATION REAGENT SYSTEMS USEFUL FOR THE MILD ONE-STEP CONVERSION OF ALCOHOLS INTO IODIDES OR BROMIDES [J].

CLASSON, B ;

LIU, ZC ;

SAMUELSSON, B .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6126-6130

[8]

DAVID S, 1992, NEW J CHEM, V16, P751

[9]

DAVID S, 1992, J CARBOHYDR RES, V230, P79

[10] AMINOSUGARS AND RELATED COMPOUNDS .6. THE ACTION OF ALKALI ON SOME BENZYLOXYCARBONYLAMINO DERIVATIVES [J].

FOSTER, AB ;

STACEY, M ;

VARDHEIM, SV .

ACTA CHEMICA SCANDINAVICA, 1959, 13 (02) :281-288

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