✦ LIBER ✦

The HCL-Catalyzed Stereomutation of Cyclic Sulfoxides

✍ Scribed by L. Sagramora; A. Garbesi; A. Fava

Publisher: John Wiley and Sons
Year: 1972
Tongue: German
Weight: 419 KB
Volume: 55
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19720550243

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✦ Synopsis

Abstract

The critical step in the HCl‐catalyzed stereomutation of sulfoxides is a nucleophilic substitution at the sulfur atom [7]. The rate of this reaction has been determined for cyclic sulfoxides as a function of ring size. The trend closely matches that long since established for substitution at alicyclic carbon [11], which confirms the similarity of the geometries of the transition states for substitution at carbon and at sulfur. The results are compared to those for the analogous silicon and phosphorous compounds, and the question of formation of pentacovalent intermediates for substitutions at sulfur is briefly discussed.

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