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Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway

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Abstract

Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran in the presence of lanthanide triflates, as well as CuOTf, Sn(OTf)2, SnCl2, ZnCl2, GaCl3, and MgI2, proceeds as a formal [3+4]-cycloaddition leading to a newly formed seven-membered ring. This reaction was found to be typical of cyclopropane-1,1-diesters and dinitriles, as well as 1-nitrocyclo-propanecarboxylates containing aromatic, heteroaromatic, and vinylic substituents at the C(2) atom of the small ring. When Me3SiOTf, TiCl4, SnCl4, or BF3·OEt2 were used as initiators, unusual cyclic hemiacetals were formed via the conjugate 1,4-addition of a cyclopropane and a nucleophile to the diene moiety.

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    A. O. Chagarovskiy, O. A. Ivanova, E. M. Budynina, E. L. Kolychev, M. S. Nechaev, I. V. Trushkov & M. Ya. Mel’nikov

  2. D. Rogachev Federal Research Center of Pediatric Hematology, Oncology, and Immunology, 1 ul. Samory Mashela, 117997, Moscow, Russian Federation

    A. O. Chagarovskiy, E. M. Budynina & I. V. Trushkov

Authors
  1. A. O. Chagarovskiy
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  2. O. A. Ivanova
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  3. E. M. Budynina
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  4. E. L. Kolychev
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  5. M. S. Nechaev
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  6. I. V. Trushkov
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  7. M. Ya. Mel’nikov
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Corresponding author

Correspondence to E. M. Budynina.

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Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2407–2423, Novemer, 2013.

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Chagarovskiy, A.O., Ivanova, O.A., Budynina, E.M. et al. Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway. Russ Chem Bull 62, 2407–2423 (2013). https://doi.org/10.1007/s11172-013-0349-x

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  • DOI: https://doi.org/10.1007/s11172-013-0349-x

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