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


  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.



Adduct Double Bond Acetylene Triplet State Acetylene Compound 
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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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