REGIOSELECTIVITY OF THE INSERTION REACTIONS OF SOME AROMATIC DIAZO COMPOUND COMPLEXES WITH CYCLOMALTOHEPTAOSE

被引：17

作者：

SMITH, SH ^{[1
]}

FORREST, SM ^{[1
]}

WILLIAMS, DC ^{[1
]}

CABELL, MF ^{[1
]}

ACQUAVELLA, MF ^{[1
]}

ABELT, CJ ^{[1
]}

机构：

[1] COLL WILLIAM & MARY,DEPT CHEM,WILLIAMSBURG,VA 23185

来源：

CARBOHYDRATE RESEARCH | 1992年 / 230卷 / 02期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0008-6215(92)84039-U

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Pyrolysis of solid complexes of aromatic diazo compounds with cyclomaltoheptaose (beta-cyclodextrin) yields ether derivatives via insertion of carbene into hydroxyl groups. The distribution of the 2-, 3-, and 6-O-isomers indicates that the regioselectivity is moderate. The guest geometry is not as important as its size in determining the ratios of regioisomers. The origins of the regioselectivity are discussed.

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收藏

页码：289 / 297

页数：9

相关论文

共 19 条

[1] STEREOSELECTIVE AZINE FORMATION IN THE DECOMPOSITION OF PHENYLDIAZOMETHANES [J].

ABELT, CJ ;

PLEIER, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1795-1799

[2] COMPLEXES OF CYCLOMALTOHEPTAOSE WITH AROMATIC DIAZO-COMPOUNDS - FORMATION AND REACTIONS [J].

ABELT, CJ ;

LOKEY, JS ;

SMITH, SH .

CARBOHYDRATE RESEARCH, 1989, 192 :119-130

[3] ARTIFICIAL ENZYMES [J].

BRESLOW, R .

SCIENCE, 1982, 218 (4572) :532-537

[4]

CREARY X, 1985, ORG SYNTH, V64, P207

[5] MINIATURE ORGANIC-MODELS OF ENZYMES [J].

DSOUZA, VT ;

BENDER, ML .

ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (04) :146-152

[6] REACTIONS OF DIMETHOXYCARBENE AND FLUOROMETHOXYCARBENE WITH HYDROXYL COMPOUNDS - ABSOLUTE RATE CONSTANTS AND THE HEAT OF FORMATION OF DIMETHOXYCARBENE [J].

DU, XM ;

FAN, H ;

GOODMAN, JL ;

KESSELMAYER, MA ;

KROGHJESPERSEN, K ;

LAVILLA, JA ;

MOSS, RA ;

SHEN, S ;

SHERIDAN, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) :1920-1926

[7] ASSOCIATION OF NAPHTHALENE AND ITS METHYL-DERIVATIVES WITH CYCLODEXTRINS IN AQUEOUS-MEDIUM [J].

FUJIKI, M ;

DEGUCHI, T ;

SANEMASA, I .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (04) :1163-1167

[8] REGIOSPECIFIC SULFONATION ONTO C-3 HYDROXYLS OF BETA-CYCLODEXTRIN - PREPARATION AND ENZYME-BASED STRUCTURAL ASSIGNMENT OF 3A,3C AND 3A,3D DISULFONATES [J].

FUJITA, K ;

TAHARA, T ;

IMOTO, T ;

KOGA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2030-2034

[9]

FUJITA K, 1984, TETRAHEDRON LETT, P5673

[10] H-1-NMR STUDY OF INTRAMOLECULAR HYDROGEN-BONDING INTERACTION IN CYCLODEXTRINS AND THEIR DI-O-METHYLATED DERIVATIVES [J].

ONDA, M ;

YAMAMOTO, Y ;

INOUE, Y ;

CHUJO, R .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (11) :4015-4021