Sonocatalysis of the TEMPO-mediated oxidation of glucosides

被引：30

作者：

Brochette-Lemoine, S ^{[1
]}

Joannard, D ^{[1
]}

Descotes, G ^{[1
]}

Bouchu, A ^{[1
]}

Queneau, Y ^{[1
]}

机构：

[1] CNRS, UMR 143, Unite Mixte Sucrochim, F-69603 Villeurbanne, France

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 1999年 / 150卷 / 1-2期

关键词：

oxidation; nitroxide; carbohydrate; sonochemistry;

D O I：

10.1016/S1381-1169(99)00197-1

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Ultrasound is shown to increase the rate of the TEMPO-mediated oxidation of methyl alpha-D-glucopyranoside or sucrose in the presence of stoichiometric amounts of sodium hypochlorite in basic aqueous medium. The reaction can then occur without the usually necessary sodium bromide, showing that ultrasound acts at the level of the formation of the nitrosonium ion, the active oxidizing species in the catalytic cycle. (C) 1999 Elsevier Science B.V. All rights reserved.

引用

页码：31 / 36

页数：6

共 27 条

[1] ANELLI PL, 1987, J ORG CHEM, V52, P2559
[2] THE CATALYTIC EFFECT OF BROMIDE IN THE HYPOCHLORITE OXIDATION OF LINEAR DEXTRINS AND INULIN
BESEMER, AC
VANBEKKUM, H
[J]. STARCH-STARKE, 1994, 46 (03): : 101 - 106
[3] DICARBOXY-STARCH BY SODIUM-HYPOCHLORITE BROMIDE OXIDATION AND ITS CALCIUM-BINDING PROPERTIES
BESEMER, AC
VANBEKKUM, H
[J]. STARCH-STARKE, 1994, 46 (03): : 95 - 101
[4] Effect of ultrasound on KSF/O mediated glycosylations
Brochette, S
Descotes, G
Bouchu, A
Queneau, Y
Monnier, N
Petrier, C
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 123 (2-3) : 123 - 130
[5] NITROXIDE-CATALYZED OXIDATION OF ALCOHOLS USING META-CHLOROPERBENZOIC ACID - NEW METHOD
CELLA, JA
KELLEY, JA
KENEHAN, EF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (12) : 1860 - 1862
[6] DAVIS NJ, 1993, TETRAHEDRON LETT, V34, P1184
[7] deNooy AEJ, 1996, SYNTHESIS-STUTTGART, P1153
[8] HIGHLY SELECTIVE NITROXYL RADICAL-MEDIATED OXIDATION OF PRIMARY ALCOHOL GROUPS IN WATER-SOLUBLE GLUCANS
DENOOY, AEJ
BESEMER, AC
VANBEKKUM, H
[J]. CARBOHYDRATE RESEARCH, 1995, 269 (01) : 89 - 98
[9] DENOOY AEJ, 1994, RECL TRAV CHIM PAY B, V113, P166
[10] DESCOTES G, 1998, CARBOHYDRATES ORGANI, V4, P39

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