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Das A, Lao EA, Gudmundsdottir AD. Photoenolization of o-Methylvalerophenone Ester Derivative. Photochem Photobiol. 2016;92(3):388-98doi: 10.1111/php.12590.
Das, A., Lao, E. A., & Gudmundsdottir, A. D. (2016). Photoenolization of o-Methylvalerophenone Ester Derivative. Photochemistry and photobiology, 92(3), 388-98. https://doi.org/10.1111/php.12590
Das, Anushree, et al. "Photoenolization of o-Methylvalerophenone Ester Derivative." Photochemistry and photobiology vol. 92,3 (2016): 388-98. doi: https://doi.org/10.1111/php.12590
Das A, Lao EA, Gudmundsdottir AD. Photoenolization of o-Methylvalerophenone Ester Derivative. Photochem Photobiol. 2016 May;92(3):388-98. doi: 10.1111/php.12590. PMID: 27061950.
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Photochem Photobiol. 2016 May;92(3):388-98. doi: 10.1111/php.12590.

Photoenolization of o-Methylvalerophenone Ester Derivative.

Photochemistry and photobiology

Anushree Das, Emily A Lao, Anna D Gudmundsdottir

Affiliations

  1. Department of Chemistry, University of Cincinnati, Cincinnati, OH.

PMID: 27061950 DOI: 10.1111/php.12590

Abstract

Photolysis of ester 1 in argon-saturated methanol and acetonitrile does not produce any product, whereas irradiation of 1 in oxygen-saturated methanol yields peroxide 2. Laser flash photolysis studies demonstrate that 1 undergoes intramolecular H atom abstraction to form biradical 3 (λmax ~340 nm), which intersystem crosses to form photoenols Z-4 and E-4 (λmax ~380 nm). Photoenols 4 decay by regenerating ester 1. With the aid of density functional theory calculations, it was concluded the photoenol E-4 does not undergo spontaneous lactonization or electrocyclic ring closure because the transition state barriers for these reactions are too large to compete with reketonization of E-4 to form 1.

© 2016 The American Society of Photobiology.

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