Trimethylsilyl phenyl selenide

Handling, Storage, and Precautions although phenyl trimethylsilyl selenide isolated as a colorless liquid is somewhat sensitive to atmospheric moisture, it can be handled conveniently using syringe techniques and can be stored indefinitely under dry nitrogen (or argon). Use in a fume hood. 

Reaction with Aldehydes and Ketones. Phenyl trimethylsilyl selenide does not react with carbonyl compounds at 25 °C or on heating. However, use of aluminum chloride as catalyst results in selective formation of selenoacetals, whereas the copresence of zinc halide in place of AICI3 leads to O-(trimethylsilyl) monoselenoacetals, which can be utilized as a-siloxy radical precursors (eq 1).  

Reaction with Acetates and Lactones. In the presence of a catalytic amount of zinc iodide, alkyl acetates and lactones react with phenyl trimethylsilyl selenide to afford alkyl phenyl selenides and )-(phenylseleno)carboxylic acids, respectively (eq2).3 

Conjugate addition of phenyl trimethylsilyl selenide to a,/3-unsaturated aldehydes and ketones has been attained by using triphenylphosphine, zinc chloride, or trimethylsilyl trifluoro-methanesulfonate as the catalyst. Combination of this reaction with selenoxide elimination provides a one-pot procedure for a-alkoxyalkylation of a,/3-unsaturated ketones (eq 3). 

Reaction with Cyclic Ethers. Ring opening of epoxides, ox-etanes, and tetrahydrofurans with phenyl trimethylsilyl selenide 

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Also widely employed are organoselenium compounds containing group 14 elements. Phenyl trimethylsilyl selenide 102 can be easily prepared from diphenyl diselenide 8 and is a good source for selenium nucleophiles (Scheme 24). In the presence of methanol selenols are generated for use in Michael reactions or in ring-... 

Although very common with a-halocarbonyl compounds, cleavage of a-oxygenated substances by nu> cleophiles is almost unknown. A mixture of phenyl trimethylsilyl selenide (38) and MgBr2 dehalogenates substituted benzoin acetates under mild conditions. The reaction probably proceeds by the HSAB path (equation 11) the precise function of MgBr is unclear. 

Phenylp-tolueneselenosulfonate, 315 Phenyl trimethylsilyl selenide, 438, 439 Phenyl vinyl sulfone, 170, 315-316 Phosphonomycin, 390 Phosphoric acid, 317 Phosphoric acid-Formic acid, 317-318 Phosphorus(III) chloride, 318 Phosphorus(III) iodide, 318-319 Phosphorus(V) oxide, 319 Phosphorus(V) sulfide, 320 Phthalides, 383... 

Phenyl trimethylsilyl selenide/magnesium bromide PhSeSiMe jMgBr2... 

The established routes to organo-selenoketones have been reviewed." New methods of preparation of these important synthetic intermediates include the oxidation of alkenes, e.g. using diphenyl diselenide, bromine, and hexabutyl-distannoxane (Scheme 2)." For terminal alkenes alternative procedures involve the intermediate formation of the corresponding bromoselenide or ethoxy-selenide the former species is converted into a phenyl selenomethyl ketone using silver hexafluorophosphate in DMSO followed by reaction with triethylamine." /3-Phenylselenoketones protected as the trimethylsilyl enol ether are available by reaction of an a/8-unsaturated ketone with phenyl trimethylsilyl selenide."... 

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