100446-40-0Relevant academic research and scientific papers
Stereoselectivity and kinetics of [4+2] cycloaddition reaction of cyclopentadiene to para-substituted E-2-arylnitroethenes
Jasinski, Radomir,Kwiatkowska, Magdalena,Baranski, Andrzej
experimental part, p. 843 - 853 (2012/06/29)
In spite of diversified electrophilicity of E-2-arylnitroethenes, their [4+2] cycloaddition reactions with cyclopentadiene leads to the corresponding 6-endo-aryl-5-exo-nitronorbornenes and 6-exo-aryl-5-endo-nitronorbornenes as the only reaction products. Stereoselectivity, substituent and solvent effects, and activation parameters, suggest that these reactions occur via a synchronous concerted mechanism on both competing pathways. The experimental results obtained are consistent with the data from B3LYP/6-31G(d) calculations. Due to high electrophilicity of E-2-arylnitroethenes, the reactions studied should be considered as polar [4+2] cycloadditions. Copyright
Synthese d'aryl nitronorbornenes par cycloaddition de Diels-Alder entre les aryl-nitroethylenes et le cyclopentadiene. Justification de la stereochimie et de la reactivite relative observees par la methode CNDO/II. Obtention d'aryl aminonorbornenes
Bourguignon, Jean,Le Nard, Gilles,Queguiner, Guy
, p. 2354 - 2361 (2007/10/02)
Syntheses of numerous 2-aryl nitroethylenes (nitrostyrenes) have been optimized.The nitrostyrenes have been reacted with cyclopentadiene in Diels-Alder cycloadditions and the 3-aryl 2-nitronorbornenes obtained have been reduced into 3-aryl 2-aminonorbornenes.These compounds are potentially dopaminergic molecules.The stereochemistry of the adducts obtained in the Diels-Alder reaction has been determined by 1H nmr.The stereochemistry and the relative reactivity of the nitrostyrenes versus cyclopentadiene have been confirmed by theoretical calculations based on the CNDO/II method.
