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Alkylating properties of alkyl fluoroalkenyl ethers

Communication 5. Reaction of alkyl perfluoroisobutenyl ethers with various nucleophiles

Conclusions

  1. 1.

    Methyl perfluoroisobutenylether exhibits alkylating properties toward pyridine, dimethylformamide and hexamethylphosphoramide. Adducts are formed as a reaction result, which contain the mesomeric perfluoroisobutenolate anion and the cation\(C_5 H_5 \mathop N\limits^ \oplus CH_3 ,(CH_3 )_2 \mathop {N = }\limits^ \oplus CHOCH_3 or [(CH_3 )_2 N]_3 \mathop P\limits^ \oplus OCH_3 .\)

  2. 2.

    The treatment of the alkyl perfluoroisobutenyl ethers with either dialkylamines or sodium alcoholates leads not to alkylation, but rather to replacement of the vinyl fluorine atom by the moiety of the nucleophile. Amino acetals and the acetals of bis(trifluoromethyl)ketene were obtained as a result.

  3. 3.

    The acetals of bis(trifluoromethyl)ketene are easily rearranged to the esters ofα-alkylhexafluoroisobutyric acids when heated in the presence of triethylamine.

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Literature cited

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Additional information

See [1] for previous communication.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1347–1353, June, 1972.

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Urushadze, M.V., Abduganiev, E.G., Rokhlin, E.M. et al. Alkylating properties of alkyl fluoroalkenyl ethers. Russ Chem Bull 21, 1298–1303 (1972). https://doi.org/10.1007/BF00854548

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Keywords

  • Acetal
  • Ether
  • Ester
  • Pyridine
  • Adduct