97567-75-4Relevant academic research and scientific papers
TELLUROXIDE ELIMINATION BY DIRECT OXIDATION OF ALKYL PHENYL TELLURIDE
Uemura, Sakae,Ohe, Kouichi,Fukuzawa, Shin-ichi
, p. 895 - 898 (1985)
Treatment of sec-alkyl phenyl tellurides, except for the cyclohexyl system, with m-chloroperbenzoic acid(MCPBA) in diethyl ether readily afforded the corresponding olefins in good yields presumably via telluroxide elimination together with small amounts of alcohols and ketones.In the pri-alkyl and cyclohexyl cases the adducts between MCPBA and the tellurides were isolated as stable organotellurium(IV) compounds which gave similar elimination products by neat pyrolysis at 220-250 deg C.
Telluroxide Elimination by Oxidation of Alkyl Aryl Tellurides: Remarkable Effect of Added Triethylamine
Nishibayashi, Yoshiaki,Komatsu, Naoki,Ohe, Kouichi,Uemura, Sakae
, p. 1133 - 1138 (2007/10/02)
Treatment of various alkyl phenyl tellurides with 1-2 mol equiv. of m-chloroperbenzoic acid in diethyl ether in the presence of triethylamine at 25 deg C for 2 h affords the corresponding alkenes highly selectively in fair to good yields.From stereochemical studies using erythro- and threo-phenyl 3-phenylbutan-2-yl tellurides as substrates it was revealed that although Et3N partly faciliates E2 elimination of the telluroxide, the main reaction course is the telluroxide syn-elimination (Ei elimination).Without the addition of Et3N the elimination was quite slow in many cases, and in fact the compounds derived from the addition of m-chlorobenzoic acid to tetradecyl and cyclohexyl phenyl telluroxides were isolated, the pyrolysis (ca. 250 deg C) of which afforded tetradec-1-ene and cyclohexene, respectively.A 2-pyridyltelluro moiety was revealed for the first time to be a better leaving group than a phenyltelluro moiety in telluroxide elimination.
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.
