The Synthesis of Sulfinylphthalimides and Their Reactions With Some Nucleophiles in Dioxane

Abstract

In this study, some N-(p-substituted-arylsulfinyl)phthalimides (1a-1e) were synthesized. The synthesized compounds were examined with respect to their substitution reactions with sodium ethoxide, sodium methoxide, methylamine, and t-butylamine in dioxane. The sub-stituent effect was investigated at 30.0 +/- 0.1 degrees C. The activation entropy was also studied, and negative Delta S-not equal values were obtained. Configuration inversions were observed in the substitution reactions. This result is in conformity with the S(N)2 mechanism. [Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: Characterization of -(p-Substituted-arylsulfinyl)phthalimides 1a-b.]