Synthetic and Mechanistic Study of Organic Reactions in the Aqueous Media

Tal Sela, Organic Chemistry, Tel Aviv Unniversity, Tel Aviv, Israel
Arkadi Vigalok, Organic Chemistry, Tel Aviv Unniversity, Tel Aviv, Israel

In addition to the environmentally benign nature of water, its beneficial effects on a variety of organic transformations have been widely recognized. Particularly, hydrophobic interactions between water and most of the organic compounds often lead to higher reactivity and/or selectivity when compared with reactions in organic media. Since the initial publications on the favorable kinetics and selectivity in the Diels-Alder cycloaddition performed in the aqueous media, many new examples of the advantages of water in various organic reactions were reported in the literature. In parallel, the mechanistic aspects of these reactions were studied in much detail. High cohesion energy density of water, hydrogen bonding-stabilized transition state, enhanced hydrophobic effect in the ground vs. transition state, were proposed as factors responsible for the reaction acceleration in the aqueous media. The purpose of our research is to establish the effect(s) of water as the reaction medium on the reactivity and selectivity of organic reactions.