69814-30-8Relevant 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.
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
N-PHENYLSELENOPHTHALIMIDE (NPSP) A VALUABLE SELENENYLATING AGENT
Nicolaou, K. C.,Petasis, N. A.,Claremon, D. A.
, p. 4835 - 4842 (2007/10/02)
The phenylseleno group (PhSe) has evolved in recent years as a very useful and versatile functionality.Its facile introduction into organic molecules and its subsequent oxidative or reductive removal, has allowed many important synthetic transformations.D
