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Synthesis and transformation of metallacycles. 25. On a mechanism of the Ni(acac)2-catalyzed conversion of 3-alkyl-1-ethylalumacyclopentanes into 1,1-disubstituted cyclopropanes

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Abstract

The reactions of 3-alkyl-1-ethylalumacyclopentanes with allyl halides in the presence of Ni(acac)2 as a catalyst were studied by dynamic NMR spectroscopy. Under the action of Ni complexes, alumacyclopentanes initially undergo intramolecular hydride transfer to give but-3-enyl(ethyl)aluminum hydrides and then react with the starting allyl halide, yielding but-3-enyl(ethyl)aluminum halides. Subsequent intramolecular carboalumination affords the corresponding 1,1-disubstituted cyclopropanes.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Bashkortostan Republic Academy of Sciences and Ufa Research Center of the Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    U. M. Dzhemilev, A. G. Ibragimov, L. O. Khafizova, L. V. Parfenova, D. F. Yalalova & L. M. Khalilov

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  1. U. M. Dzhemilev
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  2. A. G. Ibragimov
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  3. L. O. Khafizova
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  4. L. V. Parfenova
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  5. D. F. Yalalova
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  6. L. M. Khalilov
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Dzhemilev, U.M., Ibragimov, A.G., Khafizova, L.O. et al. Synthesis and transformation of metallacycles. 25. On a mechanism of the Ni(acac)2-catalyzed conversion of 3-alkyl-1-ethylalumacyclopentanes into 1,1-disubstituted cyclopropanes. Russian Chemical Bulletin 50, 1465–1468 (2001). https://doi.org/10.1023/A:1012705711678

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