59085-70-0Relevant articles and documents
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.
Preparation and oxidation of α-phenylselanyl esters
Lebarillier, Loic,Outurquin, Francis,Paulmier, Claude
, p. 7483 - 7493 (2007/10/03)
Alkylation and selenenylation of selenium-stabilized ester enolates have allowed the preparation of α-phenylselanyl esters 5, 7, 8 and of α,α-bis(phenylselanyl)esters 6, respectively. The competitive selenophilic reaction, leading to an allylic phenylselenide 9, was avoided in the presence of HMPA. α-phenylselanyl α,β-unsaturated esters 15 were prepared by oxidation of compounds 6 and dehydrohalogenation of β-chloroesters 17. Some other transformations: oxidation, transesterification and Grignard reaction were also studied. H2O2 oxidation of Z-esters 15 has led to stable E-α-seleninyl esters 20. (C) 2000 Elsevier Science Ltd.
