Structure–reactivity correlations in the aminolysis of aryl dithiomethyl-and dithiophenylacetates with anilines in acetonitrile

HK Oh, SK Kim, HW Lee, I Lee

Index: Oh, Hyuck Keun; Kim, Sun Kyung; Lee, Hai Whang; Lee, Ikchoon Journal of the Chemical Society, Perkin Transactions 2, 2001 , # 9 p. 1753 - 1757

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Abstract

The kinetics and mechanism of the anilinolysis (XC6H4NH2) of dithio esters, RC (S) SC6H4Z with R= C2H5 and C6H5CH2 are investigated in acetonitrile at 45.0° C. By application of various structure–reactivity correlations, selectivity parameters ρX, βX, ρZ, βZ and ρXZ are determined. The reactions are predicted to proceed stepwise with rate-limiting expulsion of the ArS− group. The dithio ester with R= C2H5 exhibits the fastest rate and ...

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