1,3-Cyclopentanedione Explained

1,3-Cyclopentanedione is an organic compound with the formula (CH2)3(CO)2. It is one of two isomeric cyclopentanediones, the other being 1,2-cyclopentanedione. The enol is predicted to be about 1-3 kcal/mol more stable than the diketo form.[1] The enol structure has been confirmed by X-ray crystallography.[2]

Preparation

The compound is prepared by hydrogenation of 2-cyclopentene-1,4-dione using zinc/acetic acid.[3] [4]

Notes and References

  1. 10.1021/acsomega.8b01008. DFT Study to Explore the Importance of Ring Size and Effect of Solvents on the Keto–Enol Tautomerization Process of α- and β-Cyclodiones. 2018. Jana. Kalyanashis. Ganguly. Bishwajit. ACS Omega. 3. 7. 8429–8439. 31458971. 6644555.
  2. 10.1107/S0108270189011352. Structure of 1,3-cyclopentanedione. 1990. Katrusiak. A.. Acta Crystallographica Section C: Crystal Structure Communications. 46. 7. 1289–1293.
  3. 10.1021/jo00983a027. Improved Preparation of 1,3-cyclopentanedione. 1972. McIntosh. John M.. Beaumier. Pierre.. The Journal of Organic Chemistry. 37. 18. 2905–2906.
  4. 10.15227/orgsyn.042.0036. 2-Cyclopentene-1,4-Dione. Gary H. Rasmusson. Herbert O. House. Edward F. Zaweski. Charles H. DePuy. Organic Syntheses. 1962. 42. 36.

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