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Regioselective catalytic addition of proton-donor reagents to esters of 1-alkylcyclopropene-3-carboxylic acids

2. Catalyzed reaction of methyl 1-alkylcyclopropene-3-carboxylates with hydrogen halides and carboxylic acids

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

Conclusions

  1. 1.

    It has been observed for the first time that methyl 1-alkylcyclopropene-3-carboxy-lates in the presence of 5–10 mole % of CuCl or the complex CuCl·2MeC≡CSiMe3 add hydrogen halides (HCl and HBr) and carboxylic acids with pKa values of 3–7 (monochloracetic, formic, acrylic, acetic, and permethrinic) at the C2-C3 bond with opening of the three-carbon ring to give 60–95% of the corresponding methyl E, Z-4-substituted-3-alkylbuten-3-oates in which the E-isomer predominates.

  2. 2.

    Hydrofluoric and carboxylic acids with pKa values < 3 (trifluoro-, trichloro-, and dichloroacetic acids), in the presence of 5–10 mole % of CuCl·2MeC·CSiMe3 and atmospheric moisture convert methyl l-alkylcyclopropene-3-carboxylates into the corresponding 4-alkyl-5H-furan-2-ones (yields 80–90%), no products of the additive cleavage of the three-carbon ring being present.

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Literature cited

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Authors and Affiliations

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

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

Authors
  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

For part 1, see [1].

For preliminary communication, see [2].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp, 800–806, April, 1988.

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Shapiro, E.A., Protopopova, M.N. & Nefedov, O.M. Regioselective catalytic addition of proton-donor reagents to esters of 1-alkylcyclopropene-3-carboxylic acids. Russ Chem Bull 37, 683–688 (1988). https://doi.org/10.1007/BF01455477

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  • DOI: https://doi.org/10.1007/BF01455477

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