A rational approach towards the nucleophilic substitutions of alcohols "on Water"

被引：142

作者：

Cozzi, Pier Giorgio ^{[1
]}

Zoli, Luca ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, ALMA MATER STUDIORUM, I-40126 Bologna, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 22期

关键词：

alcohols; electrophilicity scale; Friedel-Crafts reaction; heterogeneous reactions; nucleophilic substitution;

D O I：

10.1002/anie.200800622

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Walking on water: Which alcohols react with nucleophiles on the surface of water? The correlations introduced by Mayr et al., in which electrophiles are characterized by the parameter E, gives practical indications about the reactivity of alcohols with nucleophiles in pure water. Stable carbocations generated from the alcohols and characterized by E <-2.5 readily react with nucleophiles in pure water at 80°C, without added Brønsted or Lewis acids. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4162 / 4166

页数：5

共 57 条

[41]

Qin H., 2007, ANGEW CHEM, V119, P413

[42] Bismuth-catalyzed direct substitution of the hydroxy group in alcohols with sulfonamides, carbamates, and carboxamides [J].

Qin, Hongbo ;

Yamagiwa, Noriyuki ;

Matsunaga, Shigeki ;

Shibasaki, Masakatsu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (03) :409-413

[43] Formation and stability of carbocations and carbanions in water and intrinsic barriers to their reactions [J].

Richard, JP ;

Amyes, TL ;

Toteva, MM .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (12) :981-988

[44] Bronsted acid-catalyzed benzylation of 1,3-dicarbonyl derivatives [J].

Sanz, Roberto ;

Miguel, Delia ;

Martinez, Alberto ;

Alvarez-Gutierrez, Julia M. ;

Rodriguez, Felix .

ORGANIC LETTERS, 2007, 9 (10) :2027-2030

[45] Electrophilicity of 5-benzylidene-1,3-dimethylbarbituric and -thiobarbituric acids [J].

Seeliger, Florian ;

Berger, Stefan T. A. ;

Remennikov, Grygoriy Y. ;

Polborn, Kurt ;

Mayr, Herbert .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24) :9170-9180

[46] Surfactant-type bronsted acid catalyzed dehydrative nucleophilic substitutions of alcohols in water [J].

Shirakawa, Seiji ;

Kobayashi, Shu .

ORGANIC LETTERS, 2007, 9 (02) :311-314

[47] Fluorinated alcohols as solvents, cosolvents and additives in homogeneous catalysis [J].

Shuklov, Ivan A. ;

Dubrovina, Natalia V. ;

Boerner, Armin .

SYNTHESIS-STUTTGART, 2007, (19) :2925-2943

[48]

STARZYNSKI A, 2001, J CHEM ENG DATA, V46, P1627

[49] Lewis acid-catalyzed direct amination of benzhydryl alcohols [J].

Terrasson, Vincent ;

Marque, Sylvain ;

Georgy, Marie ;

Campagne, Jean-Marc ;

Prim, Damien .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) :2063-2067

[50] Facile access to optically active ferrocenyl derivatives with direct substitution of the hydroxy group catalyzed by indium tribromide [J].

Vicennati, Paola ;

Cozzi, Pier Giorgio .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (14) :2248-2253

← 1 2 3 4 5 6 →