Ketones phenyl trimethylsilyl selenide

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). ... 

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). 

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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