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Some peculiarities of the cyclization of N-polynitroalkyl-N-nitrosoaminoacetic acids and their nitriles to sydnones and sydnonimines

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Abstract

The cyclization of N-polynitroalkyl-N-nitrosoaminoacetic acids to sydnones occurs only under the influence of trifluoroacetic anhydride. Closing to a sydnonimine ring does not occur in the case of N-(2,2,2-trinitroethyl)-N-nitrosoaminoacetonitrile, but N-(2,2,2-trinitroethyl)-N-nitrosoiminoacetic acid imino ester is formed. Removal of the nitro groups in the γ position relative to the nitrosoamino group leads to normal occurrence of the reaction to give polynitroalkylsydnonimines.

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See [1] for the preliminary communication.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 335–341, March, 1974.

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Fridman, A.L., Mukhametshin, F.M., Zalesov, V.S. et al. Some peculiarities of the cyclization of N-polynitroalkyl-N-nitrosoaminoacetic acids and their nitriles to sydnones and sydnonimines. Chem Heterocycl Compd 10, 290–295 (1974). https://doi.org/10.1007/BF00472412

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  • DOI: https://doi.org/10.1007/BF00472412

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