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Reaction of 5,5'-(1,4-Phenylene)bis(3-aryl-2-oxaspiro[5.5]undec-3-en-1-ones) with Methyl 1-Bromocyclohexanecarboxylate and Zinc

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Abstract

The reaction of 3,3'-(1,4-phenylene)bis(1-phenylprop-2-en-1-ones) with the Reformatsky reagent obtained from methyl 1-bromocyclohexanecarboxylate and zinc involves addition of two molecules of the reagent to the conjugated C=C–C=O systems of the substrate. The intermediate adducts undergo intramolecular cyclization via the nucleophilic attack of the enolate oxygen atoms on the carbonyl carbon atoms. The subsequent hydrolysis of the reaction mixture resulted in the isolation of bis(spiro-3,4-dihydropyran-2-ones). The structure of the products was confirmed by X-ray diffraction.

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Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 20-33-90037).

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Authors and Affiliations

  1. Perm State National Research University, 614990, Perm, Russia

    E. A. Nikiforova, D. V. Baibarodskikh, S. N. Shurov, E. V. Kusakina & M. V. Dmitriev

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  1. E. A. Nikiforova
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  2. D. V. Baibarodskikh
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  3. S. N. Shurov
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  4. E. V. Kusakina
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  5. M. V. Dmitriev
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Correspondence to E. A. Nikiforova.

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Nikiforova, E.A., Baibarodskikh, D.V., Shurov, S.N. et al. Reaction of 5,5'-(1,4-Phenylene)bis(3-aryl-2-oxaspiro[5.5]undec-3-en-1-ones) with Methyl 1-Bromocyclohexanecarboxylate and Zinc. Russ J Org Chem 58, 249–252 (2022). https://doi.org/10.1134/S1070428022020130

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  • DOI: https://doi.org/10.1134/S1070428022020130

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