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Catalytic olefination of carbonyl compounds. Effect of the structure of the carbonyl compound on the reaction

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Abstract

The mechanism of the novel reaction of catalytic olefination of carbonyl compounds was studied. The reaction involves the transformation of hydrazones of aromatic aldehydes and ketones into the corresponding dichloroalkenes and symmetrical azines by the treatment with carbon tetrachloride in the presence of CuCl as a catalyst. The stability of intermediate diazoalkanes is the main factor determining the direction of the reaction. In the case of sufficiently stable diazoalkanes, other products can be formed under the reaction conditions along with the products of catalytic olefination.

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119992, Moscow, Russian Federation

    V. N. Korotchenko, V. G. Nenaidenko & E. S. Balenkova

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 14 Institutskii prosp., 142432, Chernogolovka, Moscow Region, Russian Federation

    A. V. Shastin

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  1. V. N. Korotchenko
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  2. A. V. Shastin
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  3. V. G. Nenaidenko
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  4. E. S. Balenkova
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Korotchenko, V.N., Shastin, A.V., Nenaidenko, V.G. et al. Catalytic olefination of carbonyl compounds. Effect of the structure of the carbonyl compound on the reaction. Russian Chemical Bulletin 52, 492–497 (2003). https://doi.org/10.1023/A:1023499925287

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