ADDITION DIPOLAIRE-1,3 AUX OLEFINS POTANT UNE SUBSTITUTION CAPTODATIVE: REACTIVITE COMPAREE DES α ET DES β AMINO ACRYLONITRILES VIS A VIS DES ARYLAZIDES.

DOI: 10.1016/S0040-4039(00)87214-7

Source and publish data:

Tetrahedron Letters p. 1893 - 1896 (1982)

Update date:2022-07-29

Topics:

Authors:

Texier, F.

Derdour, A.

Benhaoua, H.

Benabdellah, T.

Yebdri, O.

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Article abstract of DOI:10.1016/S0040-4039(00)87214-7

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.

Full text of DOI:10.1016/S0040-4039(00)87214-7

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