Structure-Reactivity Relationship of Benzyl Benzenesulfonates. Part 4. Application of Correlation Interaction Coefficients

摘要

The mechanism of nucleophilic displacement was studied by using three variable systems of ヱX, ヱ Y, and ヱZ obtained from the change of substituent X, Y, and Z for the reaction of (Z)-substituted benzyl (X)-benzensulfonates with (Y)-substituted thiobenzamides in acetone at 45 ∩. The results ヱ Z YZ ヱXZ indicate that this reaction series proceeded via a dissociative SN2 mechanism. The prediction of the movement of TS by using the sign of ヱXZ·ヱYZ accorded with the Hammond postulate.