Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water"

被引:1031
作者
Butler, Richard N. [1 ]
Coyne, Anthony G. [2 ]
机构
[1] Natl Univ Ireland, Sch Chem, Galway, Ireland
[2] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
关键词
DIELS-ALDER REACTIONS; ASYMMETRIC TRANSFER HYDROGENATION; 1,3-DIPOLAR CYCLOADDITION REACTIONS; CARBON-CARBON BOND; DIRECT ALDOL REACTIONS; COPPER-CATALYZED CYCLOADDITION; EMPLOYING STABILIZED YLIDES; TRANSITION-STATE STRUCTURES; CROSS-METATHESIS REACTIONS; PERCHLORATE-DIETHYL-ETHER;
D O I
10.1021/cr100162c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Researchers have demonstrated the comparative effects of water, which they believed is nature's reaction enforcer, for organic synthesis carried out in or on water. It was demonstrated that water was the solvent used by nature for biological chemistry. The researchers also demonstrated that successful reactions in water required the presence of buffers or catalysts and potential ungreen characteristics of reactions in water. It was demonstrated that water was highly polar solvent with a Reichardt ET(30) of 61.3, leading to acceleration of reactions with transition states more polar than initial states in water and slowed when the transition states were less polar than initial states. Organic liquids that remained separated from water in a clear organic phase were ideal reactants for such synthesis, but solids were used provided one reactant partner was a liquid and adequate mixing was ensured.
引用
收藏
页码:6302 / 6337
页数:36
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