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

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

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2020, Volume: 22, Number: 2, Pages: 604-609 Pages count : 6 DOI: 10.1021/acs.orglett.9b04376

Authors

Lvov Andrey G ^1,2 , Yadykov Anton V ² , Lyssenko Konstantin A ³ , Heinemann Frank W ¹ , Shirinian Valerii Z ² , Khusniyarov Marat M ¹

Affiliations

1	Department of Chemistry and Pharmacy, Friedrich-Alexander University Erlangen-Nürnberg (FAU), Egerlandstrasse 1, 91058 Erlangen, Germany
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prosp, 119991 Moscow, Russian Federation
3	Department of Chemistry, Lomonosov Moscow State University, 119992 Moscow, Russian Federation

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.

Lvov A.G. , Yadykov A.V. , Lyssenko K.A. , Heinemann F.W. , Shirinian V.Z. , Khusniyarov M.M.
Reversible Shifting of a Chemical Equilibrium by Light: The Case of Keto–Enol Tautomerism of a β-Ketoester
Organic Letters. 2020. V.22. N2. P.604-609. DOI: 10.1021/acs.orglett.9b04376 WOS Scopus OpenAlex

Web of science:	WOS:000508468200055
Scopus:	2-s2.0-85078331779
OpenAlex:	W2999713622

DB	Citing
OpenAlex	24
Scopus	22
Web of science	22