Journal of Organic Chemistry p. 5102 - 5109 (1981)
Update date:2022-08-02
Topics:
Counotte-Potman, Anda
Plas, Henk C. van der
Veldhuizen, Beb van
Landheer, Cees A.
3-Alkyl(aryl)-1,2,4,5-tetrazines (7) when treated with hydrazine hydrate were found to undergo a Chichibabin hydrazination into 3-alkyl(aryl)-6-hydrazino-1,2,4,5-tetrazines (8) according to an SN(ANRORC) mechanism. 1H and 13C NMR measurements indicate that the first step in this reaction sequence is the formation of a homoaromatic ? adduct anion, due to attack at C6, and that the second step is the formation of an open-chain intermediate.With 15N-labeled hydrazine, part of the label is found in the 1,2,4,5-tetrazine ring of the 6-hydrazino compounds 8*.NMR evidence is obtained which shows that the hydrazino compounds with 15N-label in the ring (8*II) and with the 15N-label in the hydrazino group (8*I) are formed according to the SN(ANRORC) mechanism.Treatment of 6-amino- or 6-halogeno-1,2,4,5-tetrazines with hydrazine leads to introducing of a hydrazino group at position 6.During this hydrazino deamination and hydrazino dehalogenation part of the molecules were found to react according to the SN(ANRORC) mechanism, the other part followed the SN(AE) pathway.
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