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1-Phenyl-1-trimethylsiloxyethylene has been used in the synthesis of β-amino ketones in water via Mannich-type reaction and cis-2,6-disubstituted dihydropyrans via three-component, one-pot cascade reaction. It is also used as chemical additives and intermediates.
Teck-Peng Loh; Lin-Li Wei. Novel one-pot Mannich-type reaction in water: Indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of β-amino ketones and esters.Tetrahedron Letters. 1998,33 323-326.
Yanlong Gu; Rodolphe De Sousa; Gilles Frapper; Christian Bachmann; Joël Barraulta and François Jérôme. Catalyst-free aqueous multicomponent domino reactions from formaldehyde and 1,3-dicarbonyl derivatives.Green Chem. 2009,11 1968-1972.
The TiCl4 promoted crossed aldol condensation with acetone illustrates the reaction of silyl enol ethers with aldehydes and ketones: Org. Synth. Coll., 8, 323 (1993). For a further example and reaction scheme, see 1-(Trimethylsiloxy)cyclohexene, A16099. For an alternative catalyst for this type of reaction, see Tetra-n-butylammonium fluoride, A10588.
ɑ-Arylation with diazonium fluoroborates to give ɑ-arylacetophenones (deoxybenzoins) occurs in pyridine, and also in other solvents in the presence of a Pd catalyst: J. Chem. Soc. Perkin 1, 283 (1994).
For a review of the synthetic applications of silyl enol ethers, see: Synthesis, 91 (1977).
Gefahrenhinweise (EU): H227-H315-H319-H335
Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.