72485-69-9Relevant academic research and scientific papers
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.
Oxidative Conversion of β-Hydroxyselenides to Epoxides and Ketones with meta-Chloroperbenzoic Acid
Uemura, Sakae,Ohe, Kouichi,Sugita, Nobuyuki
, p. 111 - 112 (2007/10/02)
Treatment of β-hydroxy-primary-alkyl and β-hydroxy-β-phenyl-primary-alkyl phenyl selenides with 3-5 equiv. of m-chloroperbenzoic acid in methanol or tetrahydrofuran gives the corresponding epoxides and phenyl migrated ketones, respectively in high yields.
STEREOCHEMICAL OUTCOME OF THE REACTION OF SOME α-SELENOALKYLLITHIUMS WITH 4-t-BUTYL CYCLOHEXANONE
Labar, D.,Krief, A.,Norberg, B.,Evrard, G.,Durant, F.
, p. 1083 - 1100 (2007/10/02)
α-selenoalkyllithiums were found to have a high propensity to add to 4-t-butyl cyclohexanone in an equatorial mode.Stereochemical assignments are discussed.
