Shrinidhi, Annadka (2017) Diels-Alder Reaction with Hydrophilic Dienes and Dienophiles. In: CHEMISTRYSELECT, 1 (12). pp. 3016-3021.
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Mechanistic aspects of the dramatic enhancement of rates of Diels-Alder reaction between some neutral substrates when carried out in water as compared to organic solvents are mainly attributed to two effects: hydrophobic effect and hydrogen bonding effect. Herein, a semi-quantitative rates approach using hydrophilic substrates in solvents of varying polarity towards the manifestation of the mechanism of water mediated Diels-Alder reaction is reported. These studies showed a relatively fast reaction in water as compared to water-organic and organic solvents therein cast doubt on the original theory of the hydrophobic effect and supports an effect similar to hydrogen bonding catalysis by water. Moreover, Diels-Alder reaction in the presence of a catalytic amount of water along with the organic solvent is more efficient as compared to the reaction in pure organic solvent and thereby further supports the hydrogen bonding effect.
| Item Type: | Journal Article |
|---|---|
| Publication: | CHEMISTRYSELECT |
| Additional Information: | Copy right for this article belongs to the WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY |
| Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
| Date Deposited: | 20 May 2017 04:08 |
| Last Modified: | 20 May 2017 04:08 |
| URI: | http://eprints.iisc.ac.in/id/eprint/56710 |
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