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Reversible Shifting of a Chemical Equilibrium by Light: The Case of Keto–Enol Tautomerism of a β-Ketoester
Organic Letters ( IF 6.555 ) Pub Date : 2020-01-07 , DOI: 10.1021/acs.orglett.9b04376
Andrey G. Lvov; Anton V. Yadykov; Konstantin A. Lyssenko; Frank W. Heinemann; Valerii Z. Shirinian; Marat M. Khusniyarov

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.
更新日期:2020-01-07

 

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