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Photochemistry of acetylenic compounds

10. Effect of temperature and substituents on the addition of 2-cyclopenten-1-one to monosubstituted acetylenes

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

Conclusions

  1. 1.

    Lowering the reaction temperature and increasing the size of the alkyl substituent in 1-alkynes substantially increases the stereospecificity of the cycloaddition of the latter to 2-cyclopenten-1-one.

  2. 2.

    The effect of substituents attached to the triple bond on the rate and stereospecificity of the cycloaddition of monosubstituted acetylene derivatives to the cyclopentenone is different from that in the case of analogous olefins.

  3. 3.

    The stereospecificity of the reaction is evidently greatly influenced by the formation of associates between the ground states of the enone and alkyne.

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Authors and Affiliations

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

    É. P. Serebryakov, S. D. Kulomzina & V. F. Kucherov

Authors
  1. É. P. Serebryakov
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  2. S. D. Kulomzina
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  3. V. F. Kucherov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 862–867, April, 1977.

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Serebryakov, É.P., Kulomzina, S.D. & Kucherov, V.F. Photochemistry of acetylenic compounds. Russ Chem Bull 26, 785–790 (1977). https://doi.org/10.1007/BF01108201

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  • DOI: https://doi.org/10.1007/BF01108201

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