Abstract
3-Amino-4-(tert-butyl-NNO-azoxy)furoxan (1a) and 4-amino-3-(tert-butyl-NNO-azoxy)-furoxan (1b) and their acetyl derivatives 6a,b were obtained. The equilibria 1a ai 1b and 6a ⇒ 6b were studied. Furoxan 6b can undergo thermal rearrangement into 3-[(tert-butyl-NNO-azoxy)(nitro)methyl]-5-methyl-1,2,4-oxadiazole (7), prolonged heating of which gives N-(2-tert-butyl-5-nitro-1-oxido-2H-1,2,3-triazol-4-yl)acetamide (8). With the transformation 7 → 8 as an example, the possibility of participation of the azoxy group in the Boulton-Katritzky rearrangements was demonstrated for the first time.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0118–0123, January, 2013.
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Zelenov, V.P., Voronin, A.A., Churakov, A.M. et al. Amino(tert-butyl-NNO-azoxy)furoxans: synthesis, isomerization, and rearrangement of N-acetyl derivatives. Russ Chem Bull 62, 117–122 (2013). https://doi.org/10.1007/s11172-013-0017-1
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DOI: https://doi.org/10.1007/s11172-013-0017-1