Abstract
Solvolysis of 1-tosyloxy-Δ2-1,2,3-triazoline-5,5-dicarboxylic acid esters (1) occurs via elimination of N2 and leads predominantly to N-β-hydroxylethyl-O-tosylhydroxylamines (II), whose structure was determined unequivocally by x-ray structural analysis. The mechanism of solvolysis of triazolines (I) is discussed, along with the structural characteristics and stabilization factors of the O-tosylhydroxylamine products (II).
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For previous communication, see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1820–1827, August, 1990.
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Shustov, G.V., Zolotoi, A.B., Belov, P.N. et al. Geminal systems. 50. Solvolysis of 1-tosyloxy-Δ2-1,2,3-triazoline-5,5-dicarboxylate esters and the structure of the solvolysis product, O-tosyl-N-α,α-bis(ethoxycarbonyl)-β-methoxyethylhydroxylamine. Russ Chem Bull 39, 1651–1657 (1990). https://doi.org/10.1007/BF00961496
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DOI: https://doi.org/10.1007/BF00961496