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Reduction of the conjugated cyclopropene bond and double bond of substituted methylenecyclopropane 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 the activated cyclopropene double bond with lithium aluminum hydride is stereospecific and leads to alcohols of the cyclopropane series even at reduced temperatures. The reaction has a high degree of regioselectivity; initial attack by the hydride ion occurs at the oxygen atom adjacent to the methoxycarbonyl group.

  2. 2.

    The reduction of functionally substituted methylenecyclopropane takes place either with retention of the exocyclic double bond or with its reduction, depending on the conditions.

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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. 1598–1604, July, 1985.

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Domnin, I.N., Dumon, K., Vincens, M. et al. Reduction of the conjugated cyclopropene bond and double bond of substituted methylenecyclopropane with lithium aluminum hydride. Russ Chem Bull 34, 1462–1467 (1985). https://doi.org/10.1007/BF00950149

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  • DOI: https://doi.org/10.1007/BF00950149

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