Direct synthesis of 3-aryl-1, 2, 4, 5-tetrazine N-1-oxides by the oxidation with methyl (trifluoromethyl) dioxirane

W Adam, C van Barneveld, D Golsch

Index: Adam, Waldemar; Van Barneveld, Claus; Golsch, Dieter Tetrahedron, 1996 , vol. 52, # 7 p. 2377 - 2384

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Citation Number: 10

Abstract

1, 2, 4, 5-Tetrazines are oxidized by methyl (trifluoromethyl) dioxirane (TFD) to their hitherto unknown1aN-oxides in excellent yields. A detailed NMR study (1H, 13C, 15N) shows that the N-1 atom of 3-aryl-1, 2, 4, 5-tetrazines 1 is oxidized regioselectively. A Hammett plot (r2= 0.970) affords a ϱ value of− 1.53. The correlation of the logarithm of the reaction rates versus the ionization potentials, which were calculated by AM1, is much worse for ...