REACTIVITY AND TAUTOMERISM OF AZOLIDINES. XXXV. DUAL REACTIVITY OF AMBIDENT ANIONS OF 2-ARYLIMINOTHIAZOLIDIN-4-ONES
The kinetics of the dual reaction of sodium salts of 2-aryliminothiazolidin-4-ones with dimethyl sulfate and methyl iodide in methanol at 25 deg C were studied.The overall methylation rate constant k1, the partial methylation constants at each reaction center k2 and k3 and their ratio k2/k3 obey the Hammet and Broensted equations.The contributions from the basicity and polarizability to the nucleophilicity of each reaction center were evaluated by means of the Edwards equation.
Ramsh, S. M.,Ginak, A. I.,Basova, Yu. G.,Shamina, L. P.
p. 742 - 747
(2007/10/02)
REACTIVITY AND TAUTOMERISM OF AZOLIDINES. XXXVI. EFFECT OF THE NATURE OF ALKYLATING AGENT AND SOLVENT ON THE DUAL REACTIVITY ON THE AMBIDENT ANIONS OF 2-ARYLIMINOTHIAZOLIDIN-4-ONES
Increase in the "hardness" of the alkylating agent leads to an increase in the degree of reaction at the cyclic nitrogen atom of the thiazolidine ring.The effect of the solvent on the direction of methylation is due to the solvating ability both with respect to the cation and with respect to the ambident anion.
Ramsh, S. M.,Ginak, A. I.,Basova, Yu. G.,Shamina, L. P.
p. 747 - 750
(2007/10/02)
REACTIVITY AND TAUTOMERISM OF AZOLIDINES. XXXIX. ALKYLATION OF ALKALI-METAL SALTS OF 2-ARYLIMINOTHIAZOLIDIN-4-ONES IN THE SOLID PHASE
The effects of the counterion, the substituted group of the alkylating agent, and the substituent at the para position of the benzene ring on the direction of alkylation of the alkali-metal salts of 2-aryliminothiazolidin-4-ones in the solid phase were investigated.The ratio of the isomeric products from alkylation at the N2' and N3 nitrogen atoms with variations of the counterion and the substituted group varies in accordance with the principle of "hard" and "soft" acids and bases.The logarithms of the N2'/N3 ratios correlate with the Hammett ? constants.
Basova, Yu. G.,Ramsh, S. M.,Ginak A. I.
p. 867 - 870
(2007/10/02)
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