An investigation of the behaviour of α,β-unsaturated sulfoxides in the presence of trimethylsilyl iodide

A mild, efficient and seemingly general method for converting α,β-unsaturated sulfoxides into carbonyl compounds by means of trimethylsilyl iodide (TMSI) is described. Experiments on different substrates and trimethylsilyl halides lead to the conclusion that the oxidation state of the sulfur atom, o...

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Bibliographic Details
Published in:Tetrahedron 2002-12, Vol.58 (51), p.10145-10150
Main Authors: Aversa, Maria C., Barattucci, Anna, Bonaccorsi, Paola, Giannetto, Placido
Format: Article
Language:English
Subjects:
carbonyl compounds
cleavage reactions
desulfurisation
sulfoxides
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Summary:A mild, efficient and seemingly general method for converting α,β-unsaturated sulfoxides into carbonyl compounds by means of trimethylsilyl iodide (TMSI) is described. Experiments on different substrates and trimethylsilyl halides lead to the conclusion that the oxidation state of the sulfur atom, on one hand, and halogen kind in TMSX on the other, assume a determining role in the progression of the reaction. The ease of experimental procedure, the possibility of 1H NMR monitoring, and good yields of final products constitute advantages of the TMSI-promoted conversion of α,β-unsaturated sulfoxides into carbonyl compounds. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)01365-0