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Intramolecular transformations of derivatives of the Michael adduct of levoglucosenone and 2-(ethoxycarbonyl)cyclododecanone. 2. Ethylene ketal and its bromination—dehydrobromination products

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Abstract

Ethylene ketal of the Michael adduct of levoglucosenone and 2-(ethoxycarbonyl)cyclo-dodecanone brominated with the system Br2—CCl4 in CHCl3 gave three types of products, namely, mono- and dibromo derivatives, as well as deprotected bromo diketone. The bromination occurred in the levoglucosenone moiety and in the cyclododecanone fragment, with the ketal protection being partially removed. Reductive debromination of difficult-to-separate di- and monobromo derivatives under the action of Zn—Bu4NI in EtOAc—EtOH and ultrasound led to the opening of the protective group dioxolane ring to give the corresponding enol ether. Treatment of the mixture of di- and monobromo derivatives with the system NaOH—EtOH or NaHCO3—DMSO triggered a stereoselective intramolecular cyclization to result in the cyclopropane and tetrahydrofuran derivatives, respectively.

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Funding

The work was carried out within the framework of the Russian state assignment (Topic Nos 122031400259-1 and 123011300044-5).

NMR spectra were recorded using the equipment of the Chemistry Center for Collective Use of the Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, and the Agidel Regional Center for Collective Use of the Ufa Federal Research Center of the Russian Academy of Sciences.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, 69 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    L. Kh. Faizullina, Yu. S. Galimova, Sh. M. Salikhov & F. A. Valeev

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  1. L. Kh. Faizullina
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  2. Yu. S. Galimova
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  3. Sh. M. Salikhov
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  4. F. A. Valeev
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Correspondence to L. Kh. Faizullina.

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The authors declare no competing interests.

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Dedicated to the memory of Academician of the Russian Academy of Sciences G. A. Tolstikov (1933–2013).

For part 1 see pp. 2411–2417.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 10, pp. 2418–2424, October, 2023.

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Faizullina, L.K., Galimova, Y.S., Salikhov, S.M. et al. Intramolecular transformations of derivatives of the Michael adduct of levoglucosenone and 2-(ethoxycarbonyl)cyclododecanone. 2. Ethylene ketal and its bromination—dehydrobromination products. Russ Chem Bull 72, 2418–2424 (2023). https://doi.org/10.1007/s11172-023-4042-4

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  • DOI: https://doi.org/10.1007/s11172-023-4042-4

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