66228-04-4Relevant articles and documents
Stereoelectronic Effect of the Trimethylsilyl Substituent upon C-O Bond Lengths at the β Position: Some Structural Studies
White, Jonanthan M.,Robertson, Glen B.
, p. 4638 - 4644 (2007/10/02)
Results of low-temperature (130 K) crystal structure analyses for seven β-trimethylsilyl-substituted cyclohexylnitrobenzoate esters are reported.For those molecules (three) with the Si-C and C-O bonds antiperiplanar the C-O bond lengths are increased by 0
Silanes in Organic Synthesis. 9. Enesilylation as a Method for 1,2-Carbonyl Migration within Ketones and for Conversion to 1,2-Transposed Allylic Alcohols
Fristad, William E.,Bailey, Thomas R.,Paquette, Leo A.
, p. 3028 - 3037 (2007/10/02)
Vinylsilanes are shown to be valuable synthetic intermediates in useful transformations of ketones.The epoxidation of vinylsilanes followed by lithium aluminium hydride reduction and oxidation with chromic acid and sulfuric acid in a two-phase (ether/water) system often gives high yields of 1,2-transposed ketones.With singlet oxygen and sequential sodium borohydride reduction, 2-trimethylsilyl alcohols are produced in which the α position of the parent ketone has been regiospecifically oxygenated.Fluoride ion promoted desilylation completes the conversion to the migrated allylic alcohol.