80447-93-4Relevant academic research and scientific papers
Direct Selenation of Electron-Rich Aromatic Compounds with (Phenylseleno)dimethylsulfonium Tetrafluoroborate
Gassman, Paul G.,Miura, Asako,Miura, Takashi
, p. 951 - 954 (2007/10/02)
(Phenylseleno)dimethylsulfonium tetrafluoroborate was found to be a highly reactive selenating agent for electron-rich aromatic compounds such as aromatic amines, phenols, and aromatic ethers.Reaction took place readily at 0-25 deg C to give ca. 50percent yields of substitution para to the activating substituent.In general, anilines gave better yields then anisoles or phenols.
Oxidation of 1,1-disubstituted hydrazines with benzeneseleninic acid and selenium dioxide. Facile preparation of tetrazenes
Back, Thomas G.,Kerr, Russell G.
, p. 2711 - 2718 (2007/10/02)
Various 1,1-disubstituted hydrazines were oxidized with benzeneseleninic acid in methanol, generally producing the corresponding tetrazenes in high yield.Studies of the by-products of the reaction, of the effects of protic vs. aprotic solvents, and trapping experiments suggest that N-aminonitrenes are unlikely intermediates in this oxidation.An alternative mechanism involving a Pummerer-like reaction of seleninamides derived from the hydrazines is proposed.Tetrazene formation fails when the hydrazine precursor contains an aryl or p-toluenesulfonyl substiuent, or when it is highly hindered.Selenium dioxide may be employed as the oxidant instead of the seleninic acid, but is generally less efficacious in achieving high tetrazene yields.
