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Reactions of alkaline-earth metal tetraethylaluminates M[Al(C2H5)4]2 with aliphatic aldehydes

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    In the reactions of alkaline-earth metal tetraethylaluminates with aliphatic aldehydes, four of the eight C2H5 groups react. The main process is alkylation with formation of a secondary alcohol.

  2. 2.

    In the reaction of lithium tetraethylaluminate with n-butyraldehyde, the main process is alkylation with the participation of two C2H5 groups, resulting in formation of a secondary alcohol; also, to a slight extent, the aldehyde is reduced with formation of 1-butanol and ethylene.

  3. 3.

    In reactions of (C2H5)3Al with aliphatic aldehydes, one alkyl group reacts, and the composition of the reaction products depends on the molar ratio RCHO: (C2H5)3Al. When the latter is 1:1, the main process is alkylation with formation of a secondary alcohol; the Oppenauer reaction and reduction occur as collateral processes. At molar ratios RCHO: (C2H5)3Al >1, the Oppenauer and Tishchenko reactions, as well as reduction, take place to a considerable extent; as a result, the yield of the secondary alcohol is substantially decreased.

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Authors
  1. L. L. Ivanov
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  2. S. Ya. Zavizion
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  3. L. I. Zakharkin
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Additional information

Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow. Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2315–2320, October, 1976.

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Ivanov, L.L., Zavizion, S.Y. & Zakharkin, L.I. Reactions of alkaline-earth metal tetraethylaluminates M[Al(C2H5)4]2 with aliphatic aldehydes. Russ Chem Bull 25, 2160–2164 (1976). https://doi.org/10.1007/BF02659539

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  • DOI: https://doi.org/10.1007/BF02659539

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