Telluroxide elimination by direct oxidation of alkyl phenyl telluride
作者:Sakae Uemura、Kouichi Ohe、Shin-ichi Fukuzawa
DOI:10.1016/s0040-4039(00)61958-5
日期:1985.1
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)
Treatment of secondary-alkyl Phenylselenides with various oxidants affords the corresponding trans-alkene highly selectively irrespective of the amount of oxidant, while in the case of the tellurium, analogues the doublebondgeometry of the product alkene depends markedly on the amount of oxidant, the trans-isomer being formed highly selectively with 1 equiv. oxidant and the proportion of the cis-isomer