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• W1567996769 abstract "The mechanism of the acid-catalysed hydrolysis of aryl-, and in particular, alkylsulfonyldiazomethanes has been studied in water, 40% (v/v) dioxan-water and 60%(v/v) dioxan-water as the solvents. The reaction is specifically catalysed by hydronium ions as indicated by the solvent deuterium isotope effect. Strong evidence is presented for carbon protonation as the first step during the hydrolysis. Very fast H-D exchange of the methine proton was observed by PMR spectroscopy in 60% (v/v) dioxan-deuterium deuterium oxide solutions of strong acids and bases. In neutral 60% (v/v) dioxan-deuterium oxide solutions the rate constants of exhange could be evaluated. The logarithm of the pseudo first order rate constants of hydrolysis are linear in H0 for CHLO4, HCI and H2SO4 as the catalysts. The slopes of these linear plots increase with increasing nucleophilicity of the conjugate base of the acid. At constant ionic strength the pseudo first order rate constants are linear in the acid concentration. At a constant HCLO4 concentration, the salts NaClO4, NaCl and NaBr showed a positive salt effect which increased with increasing nucleophilicity of the anion. In acidic media containing chloride anions, the rate enhancement as compared with solutions containing the same amount of perchlorate anions, is directly correlated to the percentage of RSO2CH2Cl formed. A bimolecular rate determining step adequately accounts for the kinetic data. The activation parameter δS‡ is also in the region of an A-2 mechanism. The nucleophilic contribution to the transition state is rather small. The oxibase scale has been used to correlate the nucleophilic sensitiveness of several diazonium ions." @default.
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• W1567996769 date "1968-01-01" @default.
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• W1567996769 title "Mechanism of reactions of α-diazosulfones—III" @default.
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• W1567996769 doi "https://doi.org/10.1016/s0040-4020(01)82480-7" @default.
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