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Regioselective catalyzed addition of proton-donor reagents to 1-alkylcyclopropene-3-carboxylate esters. 3. Reaction of methyl cyclopropane-3-carboxylates with compounds containing labile hydrogen at oxygen, sulfur, or nitrogen

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

Conclusions

  1. 1.

    Methyl 1-alkylcycloprop-3-enoates have been shown to add phenol and 4-nitrophenol in the presence of 5–100 mole% of CuCl·2MeC≡CSiMe3 at the C2-C3 bond with opening of the three-membered ring and the formation of 30–80% of the corresponding methyl Z- and E-4-phenoxy-3-alkylbut-3-enoates.

  2. 2.

    2,4-Dinitrophenol, butyl mercaptan, and 4-methylcyclohex-4-ene-1,2-dicarboximide on reaction with methyl 1-methylcyclopropene-3-carboxylate in the presence of 20–100 mole% of CuCl·2MeC≡CSiMe3 do not give addition products, functioning merely as proton donors to give the methyl Z- and E-4-chloro-3-methylbut-3-enoates in yields of up to 60%.

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Literature cited

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    E. A. Shapiro, M. N. Protopopova & O. M. Nefedov

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  1. E. A. Shapiro
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  2. M. N. Protopopova
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  3. O. M. Nefedov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2348–2352, October, 1988.

For previous communication, see [1].

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Shapiro, E.A., Protopopova, M.N. & Nefedov, O.M. Regioselective catalyzed addition of proton-donor reagents to 1-alkylcyclopropene-3-carboxylate esters. 3. Reaction of methyl cyclopropane-3-carboxylates with compounds containing labile hydrogen at oxygen, sulfur, or nitrogen. Russ Chem Bull 37, 2114–2118 (1988). https://doi.org/10.1007/BF00953416

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  • DOI: https://doi.org/10.1007/BF00953416

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