Acylcyclopentanones III-The synthesis of 2-acetylcyclopentane-1,3-diones

✍ Scribed by M. Vandewalle

• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 615 KB
• Volume: 73
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19640730530

✦ Synopsis

ACYLCYCLOPENTANONES (*) 111 -THE SYNTHESIS OF 2-ACETYLCYCLOPENTANE-1,3-DIONES (**) M. VANDEWALLE (Ghent) SUMMARY 2-Acylcyclopentane-1.3-diones and 2-acyl-4-carboethoxy-cyclopentane-1,3- diones are obtained by Dieckmann condensation of 1,4-dicarboethoxyhexane-3,Sdiones. They exist in a monoenolic form and are monobasic acids. The synthesis of 2-acylcyclopentane-1,3-diones by Dieckmann condensation has not yet been reported. Attempts to cyclize l-carboethoxyhexane-3,5-dione (IVa) were unsuccessful. It is therefore most likely that condensation of a methylene function, activated by two carbonyl groups, fails with esters other than 0 0 OH 0 a , R = H b, R=Me c, R -A d -. .