Amidoselenation of olefins via hydroxyselenation: reactions using nitriles in reagent quantity and the synthesis of β-(acrylamido)alkyl phenyl selenides

Abstract

The amidoselenation ofacrylonitrile by the β‐hydroxy selenides (I) and (V), when performed in the presence oftrifluorolnethane‐sulphonic acid, affords the β‐(acrylamido)alkyl phenyl selenides (III) and (VI) in good yields without side reactions caused by hydrogen Chloride.

New Developments with Chiral Electrophilic Selenium Reagents

“…Nitriles have been used as versatile nucleophiles in this reaction which can be converted into the corresponding amides [88,89,90]. But also other nitrogencontaining nucleophiles such as carbamates [91] or tosylamides [92] can be employed.…”

Synthesis of N-acylaziridines from β-amido selenides

“…The β-amido selenides were prepared via established procedures in two steps from the corresponding alkenes, 21,22 with overall yields of aziridine from the starting alkene at least comparable to, and in one case a six-fold improvement on, yields reported using other methods. 23, 24 Thus our methodology represents an efficient and mild alternative route to N-acylaziridines.…”

Water and Aqueous Mixtures as Convenient Alternative Media for Organoselenium Chemistry

“…The use of water in the electrophilic functionalizion of carbon-carbon multiple bonds promoted by selenium reagents is a well-known way to introduce a hydroxyl or amido group as the nucleophilic counterpart of the selenium in the attack to an olefin [48]. When the electrophile is generated in situ by the oxidation of a diselenide with ammonium persulphate, an excess of oxidant can activate the selenium moiety of the phenylselenide intermediate (12, 15) toward a deselenation process that occurs by elimination or substitution, depending on the reaction conditions and the nature of the substrates.…”