37773-29-8Relevant academic research and scientific papers
Syntheses of alkali selenolates from diorganic diselenides and alkali metal hydrides: Scope and limitations
Krief,Trabelsi,Dumont
, p. 933 - 935 (1992)
Sodium and potassium alkane[arene]selenolates have been efficiently prepared from the corresponding diselenides using sodium or potassium hydrides in dimethylformamide or tetrahydrofuran. The reaction cannot be extended for the production of their lithium analogues nor for sodium and potassium phenylmethaneselenolates.
An electrochemical method for deborylative selenylation of arylboronic acids under metal- and oxidant-free conditions
Cai, Hu,Fu, Zhengjiang,Guo, Shengmei,He, Dongdong,Yi, Xuezheng,Yin, Jian
supporting information, p. 130 - 135 (2022/01/19)
An efficient protocol to synthesize aryl selenoethers through deborylative selenylation of widely available arylboronic acids has been established under electrochemical conditions in the absence of metal catalyst and external oxidant. The synthesis of bio
Metal-Free Synthesis of Selenodihydronaphthalenes by Selenoxide-Mediated Electrophilic Cyclization of Alkynes
An, Shaoyu,Li, Pingfan,Zhang, Zhong
, p. 3059 - 3070 (2021/07/22)
A transition-metal-free, selenium mediated electrophilic cyclization reaction was realized through a one-pot procedure between simple alkynes and triflic anhydride-activated selenoxides to give selenium containing dihydronaphthalene products. This method gave good to very high yields for all products, including selenium-substituted phenanthrene, dihydroquinoline, 2H-chromene, and coumarin, which can be further transformed to other functionalized compounds.
Synthesis and Reactivity Studies of a Series of Nickel(II) Arylchalcogenolates
Cordeiro, Lauren L.,Dmitrenko, Olga,Yap, Glenn P. A.,Riordan, Charles G.
, p. 6327 - 6338 (2021/05/06)
Two series of high-spin nickel complexes, [TpPh,Me]Ni(EAr) (E = O, Se, Te; Ar = C6H5) and [TpPh,Me]Ni(SeC6H4-4-X) (X = H, Cl, Me, OMe), were prepared by metathetical reaction of the nickel(II) halide precursor with sodium salts of the corresponding chalcogen, NaEAr. X-ray crystallographic characterization and spectroscopic studies have established the geometric and electronic structures of these complexes. The observed spectroscopic and structural characteristics reveal distinct trends in accordance with the variation of the identity of the arylchalcogenolate and para substituent. Reaction of the [TpPh,Me]Ni(EAr) complexes with methyl iodide proceeded readily, producing the corresponding methylarylchalcogen and [TpPh,Me]NiI. A kinetic and computational analysis of the reaction of [TpPh,Me]Ni(SeC6H5) with MeI supports that the electrophilic alkylation reactions occur via an associative mechanism via a classical SN2 transition state.
FeCl3-Diorganyl dichalcogenides promoted cyclization of 2-alkynylanisoles to 3-chalcogen benzo[ b ]furans
Gay, Rafaela M.,Manarin, Flavia,Schneider, Caroline C.,Barancelli, Daniela A.,Costa, Michael D.,Zeni, Gilson
supporting information; experimental part, p. 5701 - 5706 (2010/10/03)
A general synthesis of 3-chalcogen benzo[b]furans from the readily available 2-alkynylanisoles, via FeCl3/diorganyl dichalcogenides intramolecular cyclization, has been developed. Aryl and alkyl groups directly bonded to the chalcogen atom were used as cycling agents. The results revealed that the reaction significantly depends on the electronic effects of substituents in the aromatic ring bonded to the selenium atom of the diselenide species. We observed that the pathway of reaction was not sensitive to the nature of substituents in the aromatic ring of anisole since both the electron-donating and the electron-withdrawing groups delivered the products in similar yields. In addition, the obtained heterocycles were readily transformed to more complex products by using a chalcogen/lithium exchange reaction with n-BuLi followed by trapping of the lithium intermediate with aldehydes, furnishing the desired secondary alcohols in good yields.
A Study of the Structure of 4-Chlorophenyl Methyl Selenide by Nuclear Magnetic Resonance of Liquid Crystalline Solutions
Avent, Anthony G.,Emsley, James W.,Longeri, Marcello,Murray, Stephen G.N.,Nicholson, Philip N.
, p. 487 - 494 (2007/10/02)
Proton and deuteron spectra of samples of 4-chlorophenylmethyl selenide dissolved in the liquid crystal solvent E9 have been recorded.Their analysis was a first step towards analysing the proton spectrum of the non-deuteriated compound, including the satellite spectra from molecules containing 7.6percent of 77Se.The dipolar couplings were used to determine the two C-Se bond lengths and to test models for the rotational potential describing the relative conformation of the phenyl ring and the C-Se-C plane.
SYNTHESIS, STRUCTURE, AND PROPERTIES OF COMPOUNDS WITH A CHALCOGEN-NITROGEN BOND. V. N-TRIFLUOROACETYL-Se-ARYL-Se-METHYLSELENIMIDES
Naddaka, V. I.,Krasnov, V. P.,Minkin, V. I.
, p. 432 - 436 (2007/10/02)
The IR and UV spectra of a series of N-trifluoroacetyl-Se-aryl-Se-methylselenimides were studied.The molecules of these compounds, like those of N-acylsulfimides and N-acyltelurimides with similar structures, have a bipolar structure, in which the negative charge is distributed through the bond system of the N-trifluoroacetyl group.
Methyl Transfers. 10. The Marcus Equation Application to Soft Nucleophiles
Lewis, Edward S.,McLaughlin, Mark L.,Douglas, Thomas A.
, p. 6668 - 6673 (2007/10/02)
The Marcus equation to methyl transfers is shown to cover reactions of " soft" nucleophiles, although small discrepancies occur.Rates and equilibria are reported for a series of reactions of arylmethylselenides with (p-chlorophenyl)dimethylselenonium ion.Experimental reaction rates between "hard" methylating agents and "soft" nucleophiles show small deviations from the calculated values, mostly but not always in the direction predicted by the HSAB principle.The Marcus equation fails to explain the previously reported "inversion" of reaction rates of 4-nitrothiophenoxide and of 4-nitrophenoxide with methyl iodide and dimethyl sulfate.Identity rates for dimethyl sulfate, methyl methanesulfonate (using 3He), methyl iodide (using 125I), and methyl triflate (using 35S) in sulfolane are reported.
Nucleophilic Aromatic Substitutions of Unactivated Aryl Halides by Methyl Selenide Anions. Synthesis and Selective Dealkylations of Aryl Alkyl Selenides
Tiecco, Marcello,Testaferri, Lorenzo,Tingoli, Marco,Chianelli, Donatella,Montanucci, Manuela
, p. 4289 - 4296 (2007/10/02)
Lithium methyl selenide, easily prepared from powdered gray selenium and MeLi, reacts with unactivated aryl halides, in DMF, to afford the aryl methyl selenides as a result of a nucleophilic aromatic substitution.The aryl methyl selenides are rapidly dealkylated in the reaction medium by MeSeLi to give the aryl selenide anions.Addition of an alkyl halide or of cyanogen iodide gives rise to the formation of aryl alkyl selenides or aryl selenocyanates in good yields.From competitive experiments, carried out on compounds of the type ArClSeR and ArClSR, it has been shown that an RSe group is as efficient as an RS group in activating the nucleophilic aromatic substitution of a chlorine atom by MeS or MeSe anions in DMF. (Alkylthio)phenyl and alkoxyphenyl alkyl selenides can be selectively dealkylated by nucleophilic aliphatic substitution with MeSNa or MeSeLi in DMF or by electron transfer with sodium in HMPA.In the first case the easiness with which the dealkylation occurs follows the order ArSeMe > ArOMe > ArSMe, whereas in the second case the order is ArSeR > ArSR > ArOR.The synthetic utility of these reactions is exemplified and discussed.
