76570-75-7Relevant academic research and scientific papers
Stereoelectronic effects in the reactivity of electrogenerated cation radicals of arylselenides
Jouikov,Fattakhova
, p. 220 - 230 (2000)
The role of stereoelectronic effects in the electrochemical oxidation of arylselenides Se-substituted by a trimethylsilylmethyl group and those with substituents bearing a carbonyl group have been considered. Although the HOMO of these compounds is formed of pz-type electrons of the ArSe moiety, the predominant contribution from the lone pair of Se makes the heteroatom more susceptible to direct electronic effects than to effects transmitted through the aromatic ring. The σ-p hyperconjugation and the interaction through space were shown to lower the charge localization on the reaction center and to stabilize cation radicals of these compounds, thus changing the control of the potential-determining reaction and promoting second order reactions.
Synthesis of 2,2-diarylvinyl phenyl selenides by dehydration of 2-hydroxyalkyl phenyl selenides
Stuhr-Hansen, Nicolai
, (2018/10/20)
A novel route to 2,2-diarylvinyl phenyl selenides is reported by dehydration of the corresponding 2,2-diaryl-2-hydroxyethyl phenyl selenides, prepared by oxyphenylselenenylations of the corresponding 1,1-diarylethylenes, upon treatment with p-toluenesulfonic acid.
Solvent-induced dichotomy in the oxidation mechanism of alkyl aromatic selenoethers
Fechete, Ioana,Jouikov, Viatcheslav
, p. 634 - 640 (2014/07/21)
Changing solvent polarity (considered in terms of dielectric permittivity ? is an easy experimental way for tuning the reactivity of electrogenerated cation radicals of alkyl aromatic selenoethers. First-order cleavage of SeC3 bond is favored in polar media, whereas bimolecular cation radical disproportionation becomes the main reaction in low-polar solvents. The key element of this dichotomy is the dielectric adjustment of specific transannular interactions between Se and CO group in the cation radicals. A series of alkyl arylselenides with pending carboxy or acetamido substituents was studied by cyclic voltammetry, IR spectroscopy and DFT calculation in binary solvents covering the span of polarity 8 2Se 2.
ANODIC PHENYLSELENYLATION OF ASYMMETRIC OLEFINS
Latypova, V. Z.,Zhuikov, V. V.,Berestovitskaya, V. M.,Kargin, Yu. M.
, p. 1517 - 1519 (2007/10/02)
The anodic phenylselenylation of asymmetric olefins is accompanied by vicinal addition of the active nucleophilic components (water, acetonitrile) at most substituted carbon atoms of the multiple bond.
Amidoselenation of Olefins and Its Utilization for Synthesis of Allylic Amides
Toshimitsu, Akio,Aoai, Toshiaki,Owada, Hiroto,Uemura, Sakae,Okano, Masaya
, p. 4727 - 4733 (2007/10/02)
The reaction of phenylselenyl chloride with olefins in acetonitrile containing trifluoromethanesulfonic acid and water affords β-acetamidoalkyl phenyl selenides in good to excellent yields.This represents the first example of one-pot amidoselenation of mono- and disubstituted olefins.The reaction can be carried out in benzonitrile, propionitrile, butyronitrile, or ethyl cyanoacetate.It was confirmed that the amidoselenation reaction proceeds with trans stereospecifity.Oxidative elimination of the produced β-amidoalkyl phenyl selenides gives allylic amides selectively in good to excellent yields.These two reactions constitute a good method for conversion of olefins to allylic amides.
Anodic acetamidoselenation of alkenes
Bewick, Alan,Coe, David E.,Fuller, Geoffrey B.,Mellor, John M.
, p. 3827 - 3828 (2007/10/02)
Anodic oxidation of diphenyldiselenide in acetonitrile in the presence of an alkene gives acetamidoselenides.
Simple Procedure for the Aminoselenation of Olefins
Toshimitsu, Akio,Aoai, Toshiaki,Uemura, Sakae,Okano, Masaya
, p. 1041 - 1042 (2007/10/02)
The reaction of phenylselenenyl chloride with olefins in acetonitrile in the presence of an acid catalyst and water is a convenient method for the aminoselenation of olefins.
