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Reaction of 2-R-naphtho[2,3-d][1,3,2]dioxaphosphinin-4-ones with arylidene derivatives of malonic acid esters: synthesis, molecular and crystal structures of 5-oxo-2-R-naphtho[2,3-f][1,2]oxaphosphepine 2-oxides

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Abstract

The reaction of 2-R-naphtho[2,3-d][1,3,2]dioxaphosphinin-4-ones with derivatives of β-dicarbonyl compounds, such as bis(2,2,3,3-tetrafluoropropyl) benzylidene- and 4-bromobenzylidenemalonates, afforded seven-membered heterocycles, 5-oxo-2-R-naphtho[2,3-f][1,2]oxaphosphepine 2-oxides, with high regioselectivity and stereoselectivity. In all cases, the major diastereomers were isolated and their structures were established by quantum chemical calculations, NMR spectroscopy, and X-ray diffraction analysis. In the crystal structures, the seven-membered heterocycle of the molecules adopts a distorted boat conformation. In solution, the molecules can adopt both a distorted boat conformation and a chair conformation with a similar energy. The process also involves the reversible kinetically controlled formation of spiro phosphoranes, which are gradually transformed into thermodynamically more stable 1,2-oxaphosphepines. The reaction proceeds under mild conditions and leads to the formation of P—C and C—C bonds and the phosphoryl group.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of Russian Academy of Sciences”, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    V. F. Mironov, M. N. Dimukhametov, Sh. K. Latypov & I. A. Litvinov

  2. A. M. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    V. F. Mironov & G. A. Ivkova

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  1. V. F. Mironov
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  2. G. A. Ivkova
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  3. M. N. Dimukhametov
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  4. Sh. K. Latypov
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  5. I. A. Litvinov
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Correspondence to V. F. Mironov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

The work was performed within the framework of the state assignments of the Kazan Scientific Center of the Russian Academy of Sciences. The synthesis of the starting compounds was performed within the framework of the Program of the Development of the Kazan (Volga Region) Federal University under the Federal Academic Leadership Programme “Priority 2030”.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 997–1011, April, 2023.

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Mironov, V.F., Ivkova, G.A., Dimukhametov, M.N. et al. Reaction of 2-R-naphtho[2,3-d][1,3,2]dioxaphosphinin-4-ones with arylidene derivatives of malonic acid esters: synthesis, molecular and crystal structures of 5-oxo-2-R-naphtho[2,3-f][1,2]oxaphosphepine 2-oxides. Russ Chem Bull 72, 997–1011 (2023). https://doi.org/10.1007/s11172-023-3865-2

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  • DOI: https://doi.org/10.1007/s11172-023-3865-2

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