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Reduction of ethyl 2-alkyl- and 2,3-dialkyl-2-cyclopropene-1-carboxylates and the corresponding cyclopropenols with lithium aluminum hydride

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

Conclusions

  1. 1.

    The reduction of ethyl 2,3-dialkylcyclopropane-1-carboxylates either take place with retention of the double bond in the ring or leads to the corresponding alcohols of the cyclopropane series, depending on the reaction conditions.

  2. 2.

    Complete reduction takes place stereospecifically; in the products the hydroxymethyl group is in the trans position in relation to the alkyl substituants.

  3. 3.

    The regioselectivity of the reduction process (the direction of initial attack by the hydride ion) is determined by the possibility of the formation of the most stable carbanion.

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Authors and Affiliations

  1. Laboratory of Dynamic and Structural Problems of Selectivity, Grenoble University, France

    I. N. Domnin, K. Dumon, M. Vincens & M. Vidal

  2. A. A. Zhdanov Leningrad State University, USSR

    I. N. Domnin, K. Dumon, M. Vincens & M. Vidal

Authors
  1. I. N. Domnin
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  2. K. Dumon
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  3. M. Vincens
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  4. M. Vidal
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1593–1598, July, 1985.

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Domnin, I.N., Dumon, K., Vincens, M. et al. Reduction of ethyl 2-alkyl- and 2,3-dialkyl-2-cyclopropene-1-carboxylates and the corresponding cyclopropenols with lithium aluminum hydride. Russ Chem Bull 34, 1457–1462 (1985). https://doi.org/10.1007/BF00950148

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  • DOI: https://doi.org/10.1007/BF00950148

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