17197-96-5Relevant articles and documents
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
2-aminopyridinium ions activate nitroalkenes through hydrogen bonding
Takenaka, Norito,Sarangthem, Robindro Singh,Seerla, Sreehari Kumar
, p. 2819 - 2822 (2008/02/07)
2-Aminopyridinium ions were found to activate nitroalkenes toward conjugate addition of heteroaromatic compounds with low catalyst loadings and the Diels Alder reaction with the periselectivity opposite to that observed with metal Lewis acids, raising the
Oxidative Addition Reactions of ω-Alkenyl Nitronate Anions
Bowman, W. Russell,Brown, David S.,Burns, Catherine A.,Crosby, David
, p. 2099 - 2106 (2007/10/02)
Anions are oxidatively added to nitronate anions to yield α-substituted nitroalkanes when potassium hexacyanoferrate(III) is used as oxidant.Oxidation of nitronate anions yields intermediate α-nitroalkyl radicals, which undergo addition by anions to give intermediate α-substituted nitroalkane radical anions, which are further oxidised to yield the α-substituted nitroalkanes.The nitronate anions used are derived from 5-nitrohex-1-ene, 6-nitrohept-1-ene, endo-5-nitro-exo-6-phenylbicyclohept-2-ene, and 1-(bicyclohept-5-en-endo-2-yl)-2-nitropropane.The intermediate α-nitroalkyl onto the ω-alkenes.The α-nitroalkyl radical derived from 1-(bicyclohept-5-en-endo-2-yl)-2-nitropropane underwent cyclisation when the oxidation was carried out in the absence of an added anion.The addition of anions (thiocyanate, benzenesulfinate, 4-chlorobenzenethiolate, and nitrite) to the α-nitroalkyl radicals derived from endo-5-nitro-exo-6-phenylbicyclohept-2-ene occurred stereoselectively from the less hindered exo face.Oxidative addition of 4-chlorobenzenethiolate to the nitronate from endo-5-nitro-exo-6-phenylbicyclohept-2-ene gave an unusual cyclisation via addition of a thiyl radical to the alkene.