Iodide-promoted deselenylation of β-chloro-and β-oxyselenides to form alkenes and selenenyl iodides
Deselenylation reaction of β-chloro-and β-oxyselenides proceeded efficiently by treatment with tetrabutylammonium iodide (TBAI) to afford alkenes in good yields. It was established that selenenyl iodides were formed in these reactions. Catalytic transformation of β-chloro-and β-oxyselenides to alkenes was also developed.
Sase, Shohei,Ebisawa, Kazuaki,Goto, Kei
supporting information; experimental part
p. 766 - 768
(2012/09/22)
Preparation of the first bench-stable phenyl selenolate: An interesting "on water" nucleophilic reagent
In this communication we report the synthesis and the characterization of the first solid and air-stable selenolates, starting from commercially available phenylselenenyl halides and elemental zinc. These reagents were efficiently employed in the ring ope
Iodosobenzene diacetate and diphenyl diselenide: An electrophilic selenenylating agent of double bonds
Phenylseleno-acetoxylation, hydroxylation, etherification and lactonization products are obtained in good yields from the reaction of alkenes with diphenyl diselenide and iodosobenzene diacetate, in acetonitrile.
Tingoli, Marco,Tiecco, Marcello,Testaferri, Lorenzo,Temperini, Andrea
p. 1769 - 1778
(2007/10/03)
SYNTHESIS OF CONJUGATED NITROALKENES VIA NITROSELENENYLATION OF ALKENES
Addition of silver nitrite to 2-bromoalkyl phenyl selenide in the presence of mercury(II)chloride afforded 2-nitroalkyl phenyl selenide, wich upon oxidative deselenenylation provided the conjugated nitroalkene in excellent yield.
SYNTHESIS OF 2-NITROALKYL PHENYL SELENIDES AND THEIR CONVERSION TO NITROALKENES
Treatment of alkenes with benzeneselenenyl bromide followed by addition of silver nitrite provided a mixture of 2-nitroalkyl and 2-hydroxyalkyl phenyl selenides.Oxidation of the former selenides with hydrogen peroxide gave nitroalkenes in 90-93 percent yields.