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Reactions of (1S,3S)-3-acetoxymethyl-1-(2-acetoxyvinyl)-2,2-dimethylcyclopropane with haloforms under conditions of phase-transfer catalysis

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Abstract

Heating of (1S,3S)-3-acetoxymethyl-1-(2-acetoxyvinyl)-2,2-dimethylcyclopropane with bromoform under phase-transfer catalysis affords dibromocyclopropane viaaddition of dibromocarbene to the double bond. In an analogous reaction with chloroform, the trichloromethyl anion adds to the double bond in the α-position with respect to the acetoxy group.

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Authors and Affiliations

  1. Ufa Research Center of the Russian Academy of Sciences, Institute of Organic Chemistry, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    M. A. Klimkin, O. S. Kukovinets, V. G. Kasradze, L. V. Spirikhin & F. Z. Galin

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  1. M. A. Klimkin
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  2. O. S. Kukovinets
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  3. V. G. Kasradze
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  4. L. V. Spirikhin
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  5. F. Z. Galin
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Klimkin, M.A., Kukovinets, O.S., Kasradze, V.G. et al. Reactions of (1S,3S)-3-acetoxymethyl-1-(2-acetoxyvinyl)-2,2-dimethylcyclopropane with haloforms under conditions of phase-transfer catalysis. Russian Chemical Bulletin 51, 1765–1767 (2002). https://doi.org/10.1023/A:1021380311747

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