Tetrahedron Letters p. 2321 - 2324 (1994)
Update date:2022-08-11
Topics:
Abramovitch, Rudolph A.
Gibson, Harry H.
Nguyen, Terry
Olivella, Santiago
Sole, Albert
4-(and 1-) Amino-1,2,4-triazoles have been treated with nitrosonium tetrafluoroborate or with isoamyl nitrile and acetic acid in the presence of mesitylene.The main product is 1,2,4-triazole, together with a small amount of the 1- and trace amounts of the 4-mesityl derivatives.Ab initio calculations of the putative 4-(1,2,4-triazoyl) cation show the electronic ground state to be a closed shell singlet 1A1 (4? e) (3), with a low-lying 3B1 triplet (4) only 1 kcal/mol above it; the ?-cation (1) is not a local minimum on the potential energy surface.Possible explanations of the results are proposed.
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