22233-90-5Relevant academic research and scientific papers
O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol
Temperini, Andrea,Siciliano, Carlo
, (2020/06/17)
A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate “in situ” benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions.
Radical intermediates in the Zn-promoted Barbier-type alkylation of diphenyl diselenide in aqueous medium
Dos Anjos, Jose Ayron Lira,Bieber, Lothar Wilhelm
, p. 6492 - 6494,3 (2012/12/12)
The zinc promoted Barbier-type reaction of alkyl halides and diphenyl diselenide in aqueous medium leads to high yields of mixed selenides even in acidic medium. Especially the efficient formation of t-butylphenylselenide cannot be explained by nucleophil
Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide: efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters
Munbunjong, Wanida,Lee, Eun Hwa,Ngernmaneerat, Poonlarp,Kim, Sung Jun,Singh, Gurpinder,Chavasiri, Warinthorn,Jang, Doo Ok
experimental part, p. 2467 - 2471 (2009/08/15)
A convenient and efficient method was developed for the synthesis of alkyl phenyl selenides, sulfides, and selenoesters in one-pot reaction by using indium metal. The reaction showed the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides. For the reaction of primary and secondary alkyl iodides and bromides, the yields of selenides were improved by the addition of a catalytic amount of iodine.
On the reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur and selenium) towards organyl halides for the synthesis of organyl phenyl chalcogenides
Peppe, Clovis,Borges De Castro, Lierson
experimental part, p. 678 - 683 (2009/10/30)
The reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur, selenium) towards organyl halides (organyl = alkyl, allyl, benzyl, acyl) was examined. A practical one-pot method to prepare organyl phenyl chalcogenides indium metal and diphenyl dichalcogenide was found. The coupling is fairly broad in scope and generally works better organyl halides capable to produce stable carbocations.
Factors controlling photochemical cleavage of the energetically unfavorable Ph-Se bond of alkyl phenyl selenides
Ouchi, Akihiko,Liu, Suyou,Li, Zhong,Kumar, S. Ajaya,Suzuki, Toshiaki,Hyugano, Takeshi,Kitahara, Haruo
, p. 8700 - 8706 (2008/03/12)
(Chemical Equation Presented) Primary photochemical paths of alkyl phenyl selenides (1) were investigated, and an origin of large deviations in the chemical yields of products obtained by carbon radical reactions induced by photolysis of phenyl selenides was clarified. KrF excimer laser photolyses of n-pentyl phenyl selenide (1a) yielded 1-pentene (2a), n-pentane (3a), n-decane (4a), dipentyl selenide (5a), benzene (6), dipentyl diselenide (7a), and diphenyl diselenide (7) as major photoproducts, with compounds 2a, 3a, 4a, 5a, and 7 formed by pentyl-Se bond cleavage, and 5a, 6, and 7a by Ph-Se bond cleavage. The selectivity of the photoproducts revealed the occurrence of an unexpected amount of Ph-Se bond cleavage (35% in n-hexane at 248 nm) during photolysis. Solvent viscosity, wavelength of light, and the structure of alkyl substituents were the major factors that controlled Ph-Se bond cleavage. The ratio of Ph-Se bond cleavage decreased with increasing solvent viscosity and laser wavelength. The effect of alkyl substituents on the ratio of bond cleavages, Ph-Se/total C-Se, was investigated for five alkyl phenyl selenides; the ratio decreased in the order pentyl > 2-methylallyl > allyl > 1-ethylpropyl > tert-butyl groups. The contribution of Ph-Se bond cleavage is most probably the origin of the large deviations in the yields of radical reactions induced by photolyses of 1, which can be minimized by selecting appropriate solvents and wavelength of light.
Zinc-mediated synthesis of tertiary alkyl selenides from tertiary alkyl halides
Krief, Alain,Derock, Michel,Lacroix, Damien
, p. 2832 - 2834 (2007/10/03)
Diorganyl selenides are efficiently synthesized from tertiary alkyl halides, selenols or selenolates and zinc dibromide as well as from diselenides in the presence of zinc. Georg Thieme Verlag Stuttgart.
Indium-mediated mild and efficient one-pot synthesis of alkyl phenyl selenides
Munbunjong, Wanida,Lee, Eun Hwa,Chavasiri, Warinthorn,Jang, Doo Ok
, p. 8769 - 8771 (2007/10/03)
A mild and convenient one-pot process for synthesizing alkyl phenyl selenides is developed using indium metal. The reaction shows the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides.
Indium(I) iodide-promoted cleavage of diaryl diselenides and disulfides and subsequent condensation with alkyl or acyl halides. One-pot efficient synthesis of diorganyl selenides, sulfides, selenoesters, and thioesters
Ranu, Brindaban C.,Mandal, Tanmay
, p. 5793 - 5795 (2007/10/03)
Diphenyl diselenides and disulfides undergo facile cleavages by indium(I) iodide and the corresponding generated selenate and thiolate anions condense in situ with alkyl or acyl halides present in the reaction mixture. Thus, a simple, efficient, and general procedure has been developed for the synthesis of unsymmetrical diorganyl selenides, sulfides (thioethers), selenoesters, and thioesters by this one-pot reaction at room temperature.
Indium(I) iodide-mediated cleavage of diphenyl diselenide. An efficient one-pot procedure for the synthesis of unsymmetrical diorganyl selenides
Ranu, Brindaban C.,Mandal, Tanmay,Samanta, Sampak
, p. 1439 - 1441 (2007/10/03)
(Matrix presented) A simple and efficient procedure has been developed for the synthesis of unsymmetrical diorganyl selenides through a one-pot indium(I) iodide-mediated reaction of alkyl halide and diphenyl diselenide in methylene chloride at room temperature.
