Summary.
The reaction between 2,2-dicyanoethenyl acylates and cyclopentadiene affords 2-acyloxy-3,3-dicyano-5-norbornene derivatives with significant stereoselectivity. Reactions between the less reactive 1,3-cyclohexadiene and anthracene require elevated temperatures and extended reaction times. Stereoselectivity of the reactions with 1,3-cyclohexadiene is higher than of those with cyclopentadiene.
Zusammenfassung.
Reaktionen zwischen 2,2-Dicyanoethenylcarbonsäureestern und Cyclopentadien ergeben mit signifikanter Stereoselektivität 2-Acyloxy-3,3-dicyan-5-norbornenderivate. Analoge Reaktionen mit den weniger reaktiven Dienen 1,3-Cyclohexadien und Anthracen erfordern höhere Temperaturen und längere Reaktionszeiten; die Stereoselektivität der Reaktionen mit 1,3-Cyclohexadien ist deutlich größer.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Author information
Authors and Affiliations
Additional information
Received November 21, 1997. Accepted December 4, 1997
Rights and permissions
About this article
Cite this article
Dees, M., Otto, HH. Diels-Alder Reactions of Push-Pull Olefins I. Reactions of Dicyanovinyl Acylates with Cyclopentadiene, 1,3-Cyclohexadiene, and Anthracene. Monatshefte fuer Chemie 129, 689–696 (1998). https://doi.org/10.1007/PL00013475
Published:
Issue Date:
DOI: https://doi.org/10.1007/PL00013475