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Homolytic addition of dichlorodibromomethane to acrylonitrile and methyl acrylate

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Conclusions

The addition of dichlorodibromomethane to acrylonitrile and methyl acrylate initiated by iron pentacarbonyl with a cocatalyst (dimethylaniline, dimethylformamide, iodine) proceeds with the rupture of the C-Br and C-Cl bonds of the addend. Three types of addition products were isolated: BrCCl2CH2CHBrX, BrCCl2CH2CHClX, and Br2CClCH2CHBrX (X=CN, COOCH3).

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Literature cited

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    M. S. Kharasch, B. M. Kuderna, and W. Urry, J. Org. Chem.,13, 895 (1948).

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    F. K. Velichko, L. V. Vinogradova, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 181 (1973).

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    M. S. Kharasch, P. S. Skell, and P. Fisher, J. Am. Chem. Soc.,70, 1055 (1948).

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1862–1865, August, 1978.

The authors thank V. I. Dostovalov for his help in running and interpreting the PMR spectra.

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Velichko, F.K., Vinogradova, L.V. Homolytic addition of dichlorodibromomethane to acrylonitrile and methyl acrylate. Russ Chem Bull 27, 1635–1638 (1978). https://doi.org/10.1007/BF00925055

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Keywords

  • Iron
  • Methyl
  • Iodine
  • Acrylate
  • Dimethylformamide