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

Published monthly
 

Michael additions of 1,3-cycloalkanediones to dimethyl acetylenedicarboxylate

P. Hrnčiar, V. Padychová, and J. Šraga

Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, CS-842 15 Bratislava

 

Abstract: Michael additions of 1,3-cyclopentanedione, 1,3-cyclohexanedione, 5,5-dimethyl-l,3-cyclohexanedione, and 1,3-cycloheptanedione to dimethyl acetylenedicarboxylate catalyzed by CH3ONa, piperidine or KF/Al203 were performed. There was found out that, like additions to a double bond, the Michael addition to a triple bond takes place successfully under KF/Al203 catalysis. The influence of a catalyst upon cis/trans ratio of the addition product was investigated; catalysis by KF/Al203  prefers the cis addition to the greater extent compared to catalysis by sodium methoxide. It was found out that the addition of 1,3-cycloheptanedione to dimethyl acetylenedicar­boxylate exhibits a more complex course of the reaction; in the case of 1,3-cyclopentanedione, the product of the trans addition does not form 2H-pyrone ring, while a derivative of 2H-pyrone is the product of trans addition of 1,3-cyclohexanediones.

Full paper in Portable Document Format: 431a87.pdf

 

Chemical Papers 43 (1) 87–95 (1989)

Sunday, July 21, 2019

IMPACT FACTOR 2018
1.246
SCImago Journal Rank 2018
0.274
SEARCH
Advanced
VOLUMES
International Conference on Coordination and Bioinorganic Chemistry
46th International Conference of SSCHE
© 2019 Chemical Papers