ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Acetylation of cyclic 1,3-diketones with isopropenyl acetate

J. Šraga and P. Hrnčiar

Department of Organic Chemistry, Komenský University, CS-842 15 Bratislava

Abstract: Reaction of 1,3-cyclopentanedione, 1,3-cyclohexanedione, 1,3-cycloheptanedione, 1,3-cyclooctanedione, 5,5-dimethyl-l,3-cyclohexanedione, and 1,3-indanedione with isopropenyl acetate afforded corresponding 3-acetoxy-2-cycloalken-l-ones in good yields. 1,3-Indanedione upon treatment with a slight excess of the acetylating reagent did not react in the expected way. Bindone was the only product of the reaction. A large excess of isopropenyl acetate had a beneficial effect on the course of the reaction. 3-Acetoxy-2-inden-l-one was the main product, accompanied with a small amount of O-acetylated bindone.

Full paper in Portable Document Format: 406a807.pdf

Chemical Papers 40 (6) 807–811 (1986)