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Hexafluoroisopropylidene and pentafluoroisopropenyl derivatives of phosphorus. Communication 2. Electrophilicity of pentafluoroisopropenylphosphonate esters and the reactions of phosphorylhexafluoroisopropyl anions

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

Conclusions

  1. 1.

    Esters of pentafluoroisopropenylphosphonic acid are similar in their electrophilic reactivity to esters of perfluoromethacrylic acid. Their reactions with alcohols and carboxylic acids give addition products while their reactions with diethylamine give vinylog substitution products. Their reactions with dimethylformamide give the product of the replacement of the CF2=group by the Me2NCH=group.

  2. 2.

    The mesomeric carbanions obtained by the addition of the fluoride anion to esters of pentafluoroisopropenylphosphonic acid readily undergo alkylation and react with carbonyl compounds in the Wittig-Horner reaction.

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Authors and Affiliations

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

    A. A. Kadyrov & E. M. Rokhlin

Authors
  1. A. A. Kadyrov
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  2. E. M. Rokhlin
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1353–1359, June, 1983.

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Kadyrov, A.A., Rokhlin, E.M. Hexafluoroisopropylidene and pentafluoroisopropenyl derivatives of phosphorus. Communication 2. Electrophilicity of pentafluoroisopropenylphosphonate esters and the reactions of phosphorylhexafluoroisopropyl anions. Russ Chem Bull 32, 1224–1230 (1983). https://doi.org/10.1007/BF00953162

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  • DOI: https://doi.org/10.1007/BF00953162

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