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Deprotonation of unsaturated fluoroethers, CH2=CHCH2OCF2CHXCF3 and CH≡CCH2OCF2CHXCF3 (X=COF and SO2F)

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

Abstract

2-Fluorocarbonyl- and 2-fluorosulfonylpentafluoropropenes upon cooling add allyl and propargyl alcohols at the C=C bond to form strong CH-acids (I)–(IV). These CH-acids react with BF3sdNEt3 under mild conditions and are converted to 2-fluorocarbonyl- and 2-fluorosulfonyl-2-trifluoromethyl-substituted unsaturated acid fluorides (V)–(VIII). The conditions, rate, and high selectivity of these reactions support the hypothesis that the formation of acid fluorides (V)–(VIII) involves a [3,3]-sigmatropic rearrangement of intermediate carbanions (Ia)–(IVa).

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Literature cited

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    V. G. Andreev, A. F. Kolomiets, A. F. Eleev & G. A. Sokol'skii

Authors
  1. V. G. Andreev
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  2. A. F. Kolomiets
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  3. A. F. Eleev
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  4. G. A. Sokol'skii
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Additional information

For preliminary communication, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1672–1675, July, 1990.

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Andreev, V.G., Kolomiets, A.F., Eleev, A.F. et al. Deprotonation of unsaturated fluoroethers, CH2=CHCH2OCF2CHXCF3 and CH≡CCH2OCF2CHXCF3 (X=COF and SO2F). Russ Chem Bull 39, 1519–1522 (1990). https://doi.org/10.1007/BF00957880

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  • DOI: https://doi.org/10.1007/BF00957880

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