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Correlation of thione-to-thiol rearrangement rates of xanthates with solvent scales. Analysis of the reaction behavior by the Kamlet-Taft parameters, π∗, α and β

✍ Scribed by Masashi Eto; Okiyasu Tajiri; Hidetoshi Nakagawa; Kazunobu Harano


Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
304 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis


The thione-to-thiol rearrangement rates for O-(2-alkenyl) (la-c), O-(l-cyclopmpylethyl) (ld) and O-(2-methylthioethyl) (le) S-methyl xanthates were analyzed by the Kamlet-Taft equation.

The results indicate that solvent polarity and solvent hydrogen-bond donation ability (acidity) are operative in the thJone-to-thiol rearrangement reactions. In the case of le, the reaction is found to be influenced by solvent acidity and retarded by the increase of the solvent polarity.