69814-30-8Relevant articles and documents
A New Route to Epoxides and Ketones by m-Chloroperbenzoic Acid Oxidation of β-Hydroxyalkyl Phenyl Selenides and Tellurides
Uemura, Sakae,Ohe, Kouichi,Sugita, Nobuyuki
, p. 1697 - 1703 (2007/10/02)
Treatment of primary (β-hydroxy)alkyl phenyl selenides with m-chloroperbenzoic acid (3-5 mol equiv.) in tetrahydrofuran or methanol gives the corresponding epoxides in high yield. cis-1-Methylene-4-t-butylcyclohexane oxide is obtained stereospecifically from 4-t-butyl-1-(phenylselenomethyl)cyclohexanol prepared by the addition of α-(phenylseleno)methyl anion to 4-t-butylcyclohexanone.On the other hand, similar oxidation of secondary (β-hydroxy)alkyl phenyl selenides affords the unexpected carboxylic acids or their esters.When a phenyl group is present on the carbon bearing the OH moiety in β-hydroxyselenides and tellurides , the oxidation is accompanied by phenyl migration to afford ketones.The reaction can be applied to one-carbon-homologated ring expansion of the benzene-ring-fused cyclic ketones by combining with the addition of an α-(phenylseleno)methyl or α-(phenyltelluro)methyl moiety to the ketones.
Regioselective Oxyselenenylation
Toru, Takeshi,Yamada, Yoshio,Maekawa, Eturo,Ueno, Yoshio
, p. 1827 - 1830 (2007/10/02)
The regioselective oxyselenenylation of terminal olefins or cycloalkenes was achieved via olefin oxymercuration and subsequent radical substitution by selenenylating reagent such as S-benzoyl Se-phenyl selenosulfide, diphenyl diselenide, or phenylselenocy
