Issue 42, 2016

Organic synthesis reactions on-water at the organic–liquid water interface

Abstract

Organic reactions that occur at the water interface for water-insoluble compounds, and reactions in water solution for water soluble compounds, has added a powerful dimension to prospects for organic synthesis under more beneficial economic and environmental conditions. Many organic molecules are partially soluble in water and reactions that appear as heterogeneous mixtures and suspensions may involve on-water and in-water reaction modes occurring simultaneously. The behavior of water molecules and organic molecules at this interface is discussed in the light of reported theoretical and experimental studies. The on-water catalytic effect, relative to neat reactions or organic solvents, ranges from factors of several hundred times to 1–2 times and it depends on the properties of reactant compounds. In some cases when on-water reactions produce quantitative yields of water-insoluble products they can reach ideal synthetic aspirations.

Graphical abstract: Organic synthesis reactions on-water at the organic–liquid water interface

Article information

Article type
Review Article
Submitted
09 Aug 2016
Accepted
30 Sep 2016
First published
30 Sep 2016

Org. Biomol. Chem., 2016,14, 9945-9960

Organic synthesis reactions on-water at the organic–liquid water interface

R. N. Butler and A. G. Coyne, Org. Biomol. Chem., 2016, 14, 9945 DOI: 10.1039/C6OB01724J

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