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Induced selectivity in the photochemistry of estrone derivatives in sustainable and micellar environment: preparative and mechanistic studies

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Abstract

In this study, we carried out preparative and mechanistic studies on the photochemical reaction of a series of 3-acylestrone derivatives in confined and sustainable micellar environment under steady-state conditions and the results were compared with those obtained in cyclohexane solution. The aim of this work is mainly focused to show whether the nature of the surfactant (cationic, neutral and anionic) leads to noticeable selectivity in the photoproduct formation. The 3-acylestrone derivatives underwent the photo-Fries rearrangement, with concomitant homolytic fragmentation of the ester group and [1;3]-acyl migration. This pathway afforded the ortho-acyl estrone derivatives, the main photoproducts together with estrone. However, epimerization of the ortho regioisomer 2-acetylestrone and estrone through Norrish Type I photoreaction occurred involving the fragmentation of the C-α at the carbonyl group (C-17) of the steroid. UV–visible and 2D-NMR (NOESY) spectroscopies have been employed to measure the binding constant Kb and the location of the steroids within the hydrophobic core of the micelle.

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Acknowledgements

SMB and JAR are research members of CONICET. MIQ thanks CONICET for doctoral scholarship

(Doctorate Program).

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Authors and Affiliations

  1. Departamento de Química Orgánica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, C1428EGA, Buenos Aires, Argentina

    Matías I. Quindt, Gabriel F. Gola, J. A. Ramirez & Sergio M. Bonesi

  2. Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), CONICET, Universidad de Buenos Aires, Ciudad Universitaria, C1428EGA, Buenos Aires, Argentina

    Matías I. Quindt & Sergio M. Bonesi

  3. Unidad de Microanálisis Y Métodos Físicos Aplicados a Química Orgánica (UMYMFOR), CONICET, Universidad de Buenos Aires, Ciudad Universitaria, C1428EGA, Buenos Aires, Argentina

    Gabriel F. Gola & J. A. Ramirez

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Supplementary file1 Time-resolved UV-visible absorption spectra of esters 1 – 3 in cyclohexane and micellar solutions. Solvent effect on the n,π* energy band from esters 1 and 2. Bathochormic and hyperchromic shifts under surfactant titration. Double-reciprocal plots for the determination of the binding constants. Comparison between 1H NMR spectra of surfactants for determination of the differential chemical shifts (Δδ).Contour plots of 2D NMR (NOESY experiments) between surfactants and esters 1 – 3. This material is available free of charge via the Internet at XXXX. (DOCX 60322 kb)

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Quindt, M.I., Gola, G.F., Ramirez, J.A. et al. Induced selectivity in the photochemistry of estrone derivatives in sustainable and micellar environment: preparative and mechanistic studies. Photochem Photobiol Sci 21, 625–644 (2022). https://doi.org/10.1007/s43630-021-00107-w

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