1694-00-4Relevant academic research and scientific papers
Aryl Arylazo Sulfones Chemistry. 2. Reactivity toward Alkaline Alkane- and Areneselenolate and Alkane- and Arenetellurolate Anions
Evers, Michel J.,Christiaens, Leon E.,Renson, Marcel J.
, p. 5196 - 5198 (2007/10/02)
Tolyl arylazo sulfones react with various alkyl- and arylseleno reagents to produce substituted alkyl aryl and unsymmetrical diaryl selenides.The corresponding tellurides can also be obtained.Isolated yields in both cases are good.This procedure is an interesting alternative to the classical Sandmeyer reaction.
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.
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.
