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Photochemistry of acetylene compounds

8. Cycloaddition of 3-methyl-3-butene-1-yne to 2-cyclohexen-1-one
  • A. Kh. Margaryan
  • É. P. Serebryakov
  • V. F. Kucherov
Organic and Biological Chemistry

Conclusions

  1. 1.

    The photocycloaddition of 3-methyl-3-buten-1-yne to 2-cyclohexen-1-one proceeds by the [2+2] scheme involving only the double bond of the enyne.

     
  2. 2.

    The resulting mixture contains six isomeric adducts derived from bicyclo[4.2.0]octan-2-one; isomers formed by head-to-tail cycloaddition predominate (about 75%); the reaction leads to the formation of a large proportion of the thermodynamically unstable isomers with transfused rings (about 51%).

     
  3. 3.

    Photocycloaddition is inhibited by additions of dimethylbutadiene and apparently proceeds via the triplet state of 2-cyclohexen-1-one.

     

Keywords

Adduct Double Bond Acetylene Triplet State Acetylene Compound 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1976

Authors and Affiliations

  • A. Kh. Margaryan
    • 1
  • É. P. Serebryakov
    • 1
  • V. F. Kucherov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic Chemistry of the Academy of Sciences of the USSRMoscow

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