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Photochemistry of acetylenic compounds. 7. Photocycloaddition of 2-cyclopentene-1-one to 1-heptyne

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Conclusions

  1. 1.

    The quantum yield of the reaction for the photocycloaddition of 2-cyclopentene-1-one to 1-heptyne (Φ=0.30±0.05) has the same order of magnitude as in the addition of (I) to disubstituted alkynes.

  2. 2.

    The reaction proceeds with the involvement of the lower triplet state of the enone and is effectively inhibited by dimethylbutadiene.

  3. 3.

    As a whole, the effect of aprotic solvents on the ratio of cycloadducts (III) and (IV) is described by the Kirkwood-Onsager equation, but the solvent effect is expressed weakly. The cycloaddition rate has a tendency to decrease with increase in the dielectric constant of the solvent.

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Literature cited

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2739–2742, December, 1975.

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Serebryakov, E.P., Kulomzina, S.D. & Kucherov, V.F. Photochemistry of acetylenic compounds. 7. Photocycloaddition of 2-cyclopentene-1-one to 1-heptyne. Russ Chem Bull 24, 2624–2627 (1975). https://doi.org/10.1007/BF01152860

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Keywords

  • Dielectric Constant
  • Quantum Yield
  • Alkyne
  • Triplet State
  • Solvent Effect