BASICITY, NUCLEOPHILICITY, AND NUCLEOFUGALITY IN THE ELIMINATION-SUBSTITUTION REACTIONS OF BETA-PHENYLMERCAPTOETHYL PHENOLATES IN DMSO-ETHANOL MEDIA

Authors
  1. Xie, H-Q.
  2. Truong, N.
  3. Buncel, E.
Corporate Authors
Defence Research Establishment Suffield, Ralston ALTA (CAN);Queen's Univ, Kingston ONT (CAN) Dept of Chemistry
Abstract
Kinetic studies have been performed on the base-promoted 1,2-elimination reactions of a series of Beta-phenlymercaptoethyl phenolates with potassium ethoxide in EtOH-DMSO media, yielding phenyl vinyl sulfide. The E2 mechanism was indicated by the absence of H/D exchange in the substrate when the reaction in EtOD-DMSO-d6 contaiing EtO(-) was carried to partial completion. The Bronsted coefficient values (Beta LG, effect of nucleofugality on reaction rate) of ca. 0.30 and ca. 0.98 were estimated for the reaction in pure DMSO and ethanol, respectively. Comparison of the results with reported reactions of substrates of similar structure revealed the important role of the phenyl group on sulfur, the leaving-group nulceofugality, and the medium basicity, in controlling the reaction pathways (elimination versus substitution).
Date of publication
26 Mar 1993
Number of Pages
6
Reprinted from
Can of Chem, vol 72, 1994, p 448-453
DSTKIM No
94-03760
CANDIS No
143427
Format(s):
Hardcopy;Originator's fiche received by DSIS

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