Title

Use of Broensted Relationship to Detect a Mechanistic Shift for Reaction of 2-(methylthio)ethyl Chloride with Thiophenoxide Anions

Abstract

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.

Document Type

Article

DOI

https://doi.org/10.1021/jo00251a055

Publication Date

8-1-1988

Journal Title

Journal of Organic Chemistry

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