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The HCL‐Catalyzed Stereomutation of Cyclic Sulfoxides
Author(s) -
Sagramora L.,
Garbesi A.,
Fava A.
Publication year - 1972
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19720550243
Subject(s) - chemistry , alicyclic compound , sulfur , catalysis , nucleophilic substitution , transition state , substitution (logic) , ring (chemistry) , carbon fibers , carbon atom , substitution reaction , medicinal chemistry , organic chemistry , materials science , composite number , computer science , composite material , programming language
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.