Reversible Shifting of a Chemical Equilibrium by Light: The Case of Keto-Enol Tautomerism of a β-Ketoester

Lvov AG, Yadykov AV, Lyssenko KA, Heinemann FW, Shirinian VZ, Khusniyarov M (2020)

Publication Type: Journal article

Publication year: 2020

Journal

Organic Letters American Chemical Society

DOI: 10.1021/acs.orglett.9b04376

Abstract

Manipulating the equilibrium between a ketone and an enol by light opens up ample opportunities in material chemistry and photopharmacology. By incorporating β-ketoester into the ethene bridge of a photoactive diarylethene, we achieved reversible light-induced tautomerization to give thermally stable enol. In a pristine state, the tautomeric equilibrium is almost completely shifted toward the ketone. Photocyclization of diarylethene results in a new equilibrium containing a significant fraction of the enol tautomer.

Authors with CRIS profile

Frank Wilhelm Heinemann Lehrstuhl für Anorganische und Allgemeine Chemie Marat Khusniyarov Lehrstuhl für Anorganische und Allgemeine Chemie

Involved external institutions

Zelinsky Institute of Organic Chemistry RU Russian Federation (RU) Lomonosov Moscow State University / Московский государственный университет имени М.В.Ломоносова RU Russian Federation (RU)

How to cite

APA:

Lvov, A.G., Yadykov, A.V., Lyssenko, K.A., Heinemann, F.W., Shirinian, V.Z., & Khusniyarov, M. (2020). Reversible Shifting of a Chemical Equilibrium by Light: The Case of Keto-Enol Tautomerism of a β-Ketoester. Organic Letters. https://doi.org/10.1021/acs.orglett.9b04376

MLA:

Lvov, Andrey G., et al. "Reversible Shifting of a Chemical Equilibrium by Light: The Case of Keto-Enol Tautomerism of a β-Ketoester." Organic Letters (2020).

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