82936-40-1Relevant academic research and scientific papers
ADDITION DIPOLAIRE-1,3 AUX OLEFINS POTANT UNE SUBSTITUTION CAPTODATIVE: REACTIVITE COMPAREE DES α ET DES β AMINO ACRYLONITRILES VIS A VIS DES ARYLAZIDES.
Texier, F.,Derdour, A.,Benhaoua, H.,Benabdellah, T.,Yebdri, O.
, p. 1893 - 1896 (1982)
Arylazides reacted with α amino-acrylonitriles 1 to produce 1-aryl-5-amono-triazoles, and with β amiono-acrylonitriles 2 to give 1-aryl-4-cyano-triazoles.Kinetics showed the Hammett ρ to be > ? and therefore, these reactions are controlled by LUMOazide-HOMOolefin interaction.Despite the captodative substitution in 1, the very small reactivity difference observed between the two isomers 1 and 2 (ΔΔE ca 500 cal.M-1) does'nt agree with a diradical intermediate.
Arylazide additions to α- and β- aminoacrylonitriles: Synthesis of 5-amino and 4-cyano-1,2,3-triazoles. Kinetic study of the cycloaddition
Derdour, A.,Benabdallah, T.,Merah, B.,Texier, F.
, p. 69 - 78 (2007/10/02)
Arylazides reacted with α-aminoacrylonitriles 1 (captodative olefins) to produce in excellant yields 5-amino-1-aryl-1,2,3-triazoles.HCN was spontaneously eliminated from the corresponding triazoline.Reaction of the same 1,3-dipoles with β-aminoacrylonitri
