Use of Broensted Relationship to Detect a Mechanistic Shift for Reaction of 2-(methylthio)ethyl Chloride with Thiophenoxide Anions
The linear Brønsted plot for reaction of thiophenoxide ions with 2-(methylthio)ethyl chloride in DMSO changes slope for highly deactivated thiophenoxides, thus suggesting a mechanism change. Attack of a neutral nucleophile on an anionic electrophile may be involved.
Harris, J. Milton, M. R. Sedaghat-Herati, and Samuel P. McManus. "Use of Broensted relationship to detect a mechanistic shift for reaction of 2-(methylthio) ethyl chloride with thiophenoxide anions." The Journal of Organic Chemistry 53, no. 16 (1988): 3893-3894.
Journal of Organic Chemistry