Tetrahedron Letters p. 1893 - 1896 (1982)
Update date:2022-07-29
Topics:
Texier, F.
Derdour, A.
Benhaoua, H.
Benabdellah, T.
Yebdri, O.
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.
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Doi:10.1248/cpb.30.2410
(1982)Doi:10.1246/cl.1982.1151
(1982)Doi:10.1016/S0040-4039(00)87507-3
(1982)Doi:10.1002/jps.2600810216
(1992)Doi:10.1016/S0040-4039(00)88440-3
(1982)Doi:10.1002/ejoc.202100205
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