Organosilane-Induced Synthesis and Functionalization of Sulfur-Containing Compounds
✍ Scribed by Alessandro Degl’Innocenti; Antonella Capperucci
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 766 KB
- Volume
- 2000
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Reactions of organothiosilanes with organic substrates generally lead to delivery of a sulfur moiety onto the target molecule, the precise outcome being related to the structure of the silyl sulfide used. Aromatic and aliphatic silyl sulfides react with carbonyl compounds under acidic or basic conditions to afford thioacetals and thioketals, but reactions with more activated compounds such as α,β-unsaturated acylsilanes give the Michael adducts, which represent versatile intermediates in organic synthesis. Silyl sulfides can also participate in substitution reactions of silyl enol ethers to afford vinyl sulfides. On the contrary, hexamethyldisilathiane reacts with various carbonyl compounds under the catalysis of CoCl 2 ⋅6H 2 O or CF 3 SO 3 SiMe 3 with thionation of the carbonyl unit, thereby providing a general access to thioketones and thioaldehydes, which can be MICROREVIEWS: This feature introduces the readers to the authors' research through a concise overview of the selected topic. Reference to important work from others in the field is included.
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