ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Electrosynthesis of (E)-Ethenyl-O-ethyl-thiocarbonatesElectrochemical reductions of 4-aryl- and 4,5-diaryl-1,2,3-thiadiazols (1-5) in acetonitrile/0,1 M tetraalkylammonium-supporting-electrolyte at Hg-cathodes in the presence of ethylchloroformiate (CAE) yield (E)-S-(2-aryl) ethenyl- and S-(1,2-diaryl)ethenyl-O-ethyl-thiocarbonates (1a-5a). The S-carboxylation proceeds via preformation of cyclic-voltammetric- and 1H-nmr-provable CAE-complexes, ring-opening and N2-elimination in a two-electron reduction. The synthesis including a rearrangement of a N-tos-S-CAE-complex is discussed in context with CNDO/2 quantum chemical calculation. Thermochemical synthesis of this new class of thiocarbonates proved unsuccessful.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19913330613
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