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Synthesis and Electrohydrodimerization of meta ‐Substituted Thiocinnamic Acid S ‐Esters
Author(s) -
Gruber Jonas,
Camilo Fernanda F.,
Arantes Ana C. M.
Publication year - 1999
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/(sici)1522-2675(19990310)82:3<389::aid-hlca389>3.0.co;2-m
Subject(s) - chemistry , solvent , polar , coupling constant , cathodic protection , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , electrochemistry , electrode , physics , particle physics , astronomy
The synthesis of the novel m ‐substituted S ‐methyl thiocinnamates 1 – 4 is described. Cathodic reductions of S ‐esters 1 – 3 , carried out at constant potentials corresponding to their first voltammetric E pc , in a polar aprotic solvent, led exclusively to the racemic `all‐ trans '‐configured 2,3‐diaryl‐5‐oxocyclopentane‐1‐carbothioates, as shown by assignments of 1 H‐NMR coupling constants.