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Action of magnesium on polyhaloalkanes and polyhaloalkenes and synthesis of 5, 5-dichloropentaneboronic acid

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

Conclusions

  1. 1.

    The bromides CHCl2(CH2)nCH2Br and CCl2=CH(CH2)nBr, where n=3 and 5, react with magnesium in ether to give ω,ω-dichloroalkyl (alkenyl)magnesium bromides, in yields of 40–50% for n=3, and 10–20% for n=5. The condensation products [CHCl2(CH2)nCH2-]2 and [CCl2=CH(CH2)n-]2 are also formed in 10–30% of the theoretical yields.

  2. 2.

    5, 5-Dichloropentaneboronic acid, identified as the iminodiethyl ester, was synthesized from the Grignard reagent, obtained from 1, 1-dichloro-5-bromopentane and magnesium.

  3. 3.

    Bromides of the type CHCl2(CH2)nCH2Br and CC12=CH(CH2)nBr, where n=3 and 5, were obtained from the corresponding chlorides by exchange of the chlorine in the CH2Cl group by bromine.

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, USSR

    N. V. Kruglova & R. Kh. Freidlina

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  1. N. V. Kruglova
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  2. R. Kh. Freidlina
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1028–1032, May, 1971.

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Kruglova, N.V., Freidlina, R.K. Action of magnesium on polyhaloalkanes and polyhaloalkenes and synthesis of 5, 5-dichloropentaneboronic acid. Russ Chem Bull 20, 943–947 (1971). https://doi.org/10.1007/BF00862200

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  • DOI: https://doi.org/10.1007/BF00862200

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