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Some Peculiarities of Bromination of 3-(Methylfuryl)-3-(diehoxyphosphoryl)acrylates with N-Bromosuccinimide Under the Conditions of Radical Initiation

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Abstract

Bromination of 3-(methylfur-2-yl)- and 3-(methylfur-3-yl)-3-(diethoxyphosphoryl) acrylates with N-bromosuccinimide in carbon tetrachloride in the presence of azobisisobutyronitrile (AIBN) as a source of radicals is studied. It was found that if at least one α-position of the furan ring is free, the first bromine atom enters exactly there, and only after that bromination of the methyl group takes place. If both α-positions are free, the bromine atom first enters the position with the most high electron density, then the remaining α-position, and only after that bromination of methyl group takes place. The reaction rates differ significantly, therefore, it is possible to isolate in the pure state the compounds containing one, two, and three bromine atoms.

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REFERENCES

  1. Pevzner, L.M., Ignat’ev, V.M., and Ionin, B.I., Zh. Obshch. Khim., 1998, vol. 68, no. 4, p. 579.

    Google Scholar 

  2. Pevzner, L.M., Russ. J. Gen. Chem., 2016, vol. 86, no. 7, p. 1624. https://doi.org/10.1134/S107036321607015X

    Article  CAS  Google Scholar 

  3. Naganawa, A., Ichikawa, Y., and Isobe, M., Tetrahedron, 1994, vol. 50, no. 30, p. 8969. https://doi.org/10.1016/S0040-4020(01)85365-5

    Article  CAS  Google Scholar 

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Funding

The work was carried out within the framework of the state assignment of the Ministry of Science and Higher Education of the Russian Federation no. 785.00.X6019 using the equipment of the engineering center of the St. Petersburg State Technological Institute (Technical University), as well as with the support of the Russian Foundation for Basic Research (grant no. 19-08-01232).

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  1. St. Petersburg State Institute of Technology (Technical University), 190013, St. Petersburg, Russia

    L. M. Pevzner

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  1. L. M. Pevzner
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Correspondence to L. M. Pevzner.

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Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 6, pp. 896–908 https://doi.org/10.31857/S0044460X2106007X.

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Pevzner, L.M. Some Peculiarities of Bromination of 3-(Methylfuryl)-3-(diehoxyphosphoryl)acrylates with N-Bromosuccinimide Under the Conditions of Radical Initiation. Russ J Gen Chem 91, 1016–1027 (2021). https://doi.org/10.1134/S1070363221060074

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  • DOI: https://doi.org/10.1134/S1070363221060074

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