Collect. Czech. Chem. Commun. 2010, 75, 919-929
Published online 2010-09-09 06:47:02

Conjugated nitroalkenes in cycloaddition reactions. Part 2. Diels–Alder reactions of E-2-aryl-1-cyano-1-nitroethenes with cyclopentadiene

Radomir Jasiński*, Michał Rzyman and Andrzej Barański

Institute of Organic Chemistry and Technology, Cracow University of Technology, 31-155 Kraków, Poland


The reaction between E-2-aryl-1-cyano-1-nitroethenes 1a1e and cyclopentadiene (2) occurs according to the carbodiene [4+2]cycloaddition scheme and leads to the corresponding 6-endo-aryl-5-endo-cyano-5-exo-nitronorbornenes 3a3e and 6-exo-aryl-5-exo-cyano-5-endo-nitronorbornenes 4a4e as the only reaction products. The attempts to detect the products of heterodiene [4+2]cycloaddition in the reaction environment were not successful.

Keywords: [4+2]Cycloaddition; Nitroalkenes; Cyclopentadiene; Nitronorbornenes; Diels– Alder reaction; Carbocycles; Heterocycles.

References: 22 live references.