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

Solvolysis of 1-tosyloxy-²-1,2,3-triazoline-5,5-dicarboxylic acid esters (1) occurs via elimination of N₂ and leads predominantly to N--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).For previous communication, see 1].Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1820–1827, August, 1990.